text:
Archaeologists Discover Earliest Example Of Dog Domestication In Arabia
By Mary Louise Kelly,
Ari Shapiro, Patrick Jarenwattananon, Anna Sirianni
When archaeologists in Saudi Arabia excavated an ancient tomb, they were expecting to find the remains of a man. They weren't expecting to find man's best friend - bone fragments of a dog laid to rest with humans.
HUGH THOMAS: The animal bones had signs of age on it, like arthritis, which suggests that the dog had lived a pretty decent, long life. This was the first sign that we had of domestic dog.
Hugh Thomas. He led the research team. Given how old the tomb was, he suspected it might have been a historically early example of a pet dog. But this was March 2020, and before they could determine when the dog lived, the pandemic hit.
THOMAS: Just as we were finding out this amazing discovery, we actually had to leave Saudi Arabia very quickly and return back home.
SHAPIRO: Thomas was finally able to run tests on a bone fragment this year.
THOMAS: This little piece of dog jaw bone, being able to get it tested, having that date come back, it was an incredibly exhilarating moment because suddenly it dawned on us, you know, wow, do we have the oldest domesticated dog in Arabia?
SHAPIRO: They did. The remains turned out to be 6,000 years old.
KELLY: And once researchers knew when the dog lived, they wanted to know how the dog lived. So they looked to rock art, paintings and etchings on slabs of rock. Each image is a clue about what life was like back then, says archaeologist Maria Guagnin.
MARIA GUAGNIN: There's always been this debate. How much control did humans actually have over these dogs? Just from bone remains, you can't really answer that question. And in the rock art, we could see there were leashes. And there was clear control over dogs. And different dogs had different roles in hunting strategies.
KELLY: The rock art shows some dogs looking fierce and barking, while others look more timid. Those subtle differences suggest domestication.
GUAGNIN: Each dog is different, and you can see their character coming through, even in sort of simple rock art depictions. You can really see that these people that depicted them had a personal relationship with each dog and knew each dog.
SHAPIRO: Six thousand years later, researcher Hugh Thomas knows something about that special relationship.
THOMAS: We have two little lap dogs, two pugs called Mixi (ph) and Aya (ph). Certainly, they would not be able to survive in that landscape.
SHAPIRO: Pugs may not be so helpful with hunting or survival in the desert, but just like those ancient Arabian dogs, they still make good companions. Transcript provided by NPR, Copyright NPR.
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Mary Louise Kelly is a co-host of All Things Considered, NPR's award-winning afternoon newsmagazine.
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DOI: 10.1039/C9SC05196A (Edge Article) Chem. Sci., 2020, Advance Article
Development of copper-catalyzed enantioselective decarboxylative aldolization for the preparation of perfluorinated 1,3,5-triols featuring supramolecular recognition properties†
Céline Sperandio, Jean Rodriguez and Adrien Quintard *
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France. E-mail: adrien.quintard@univ-amu.fr; Web: http://ism2.univ-amu.fr/fr/annuaire/stereo/quintardadrien
Received 14th October 2019 , Accepted 17th December 2019
First published on 27th December 2019
Fluorine is able to confer unique properties to organic molecules but the scarcity of natural organofluorine sources renders the development of new synthetic methods highly desirable. Using a chiral BOX/Cu combination, enantioselective decarboxylative aldolization of perfluorinated aldehydes has been developed. Most notably, the reaction occurring under mild conditions and with high enantiocontrol can create ketodiols in one single synthetic operation, which are precursors of crucial perfluorinated 1,3,5-triols. In addition, the reaction performed with chloral, validates the proposed transition state model based on steric interactions and provides the first enantioselective synthesis of hexachlorinated ketodiol of great synthetic utility. The ability of perfluorinated 1,3,5-triols to form a central hydrogen-bonding framework allows strong coordination of anions and the chirality obtained through the catalyst-controlled synthetic sequence demonstrates the selective chiral anion recognition ability of polyols.
Organic molecules efficient in selective supramolecular recognition are central to numerous drugs, nano-devices, catalysts and materials.1 As a result, chemist's ability to design and prepare host molecules with improved binding affinities and selectivities is crucial. However, the preparation of original molecular objects has for long remained limited by the availability of starting materials or current existing synthetic methods. This is especially true regarding fluorine containing molecules, notably the ones possessing strong electron-withdrawing perfluorinated chains ((CF2)n-CF3), able to confer unique properties to numerous drugs, materials and catalysts.2 While fluorine insertion can impressively improve these supramolecular interactions, the preparation of these molecules depends exclusively on the synthetic chemist's ability to accommodate this particular atom through a reliable synthetic route, rendering the discovery of original synthetic methods of great value.3
Given the progress made in the last few decades towards more efficient synthesis thanks to catalysis,4 it should now be possible to conceive on a routine basis the de novo design and synthesis of improved molecular objects through the parallel on demand development of original catalytic methods.
Among potential motifs for host molecule design, acyclic alcohols are particular due to the relatively weak interactions provided by a single alcohol hydrogen bond. This is why despite their ubiquity in numerous highly bioactive natural products and drugs, synthetic flexible acyclic polyols have only been identified recently for their coordination and catalytic properties.5 It was shown notably by the group of Kass that multiplication of alcohol functionalities5e–g or insertion of adjacent CF3 groups6 could increase the H-bonding strength of the core alcohol H-bonding frameworks. This role of the CF3 substituents in alcohol properties is further highlighted by the unique reactivity promoted by the use of hexafluoroisopropanol (HFIP) as the solvent.7 However, the enantioselective elaboration of perfluorinated alcohols still constitutes a major synthetic challenge. This considerably limits the construction of new scaffolds featuring enhanced supramolecular chiral recognition properties. As a result, designing new types of chiral perfluorinated alcohols and discovering new approaches for their enantioselective preparation is highly desirable.
In this context, we hypothesized that combining a central chiral 1,3,5-triol motif with adjacent electron-withdrawing perfluorinated chains would provide innovative molecules for application in selective supramolecular recognition by anion binding (Scheme 1a). These molecules would bridge the gap between known achiral or racemic flexible acyclic alcohols5,6 and more classical chiral receptors8 with strong implications in anion coordination or catalysis.
Scheme 1 Proposed enantioselective approach towards perfluorinated 1,3,5-triols and their supramolecular coordination properties.
In addition, in order to readily prepare these chiral complex molecules, we desired to perform parallel development of an original and modular enantioselective catalyst-controlled method also amenable to target other scaffolds of interest (Scheme 1b).
Herein, we report our success at fulfilling this double goal of constructing rapidly and with excellent stereocontrol the desired perfluorinated 1,3,5-triols with enhanced supramolecular properties starting from bio-sourced 1,3-acetonedicarboxylic acid through stereocontrolled bi-directional decarboxylative aldolization (Scheme 1b).
Development of catalytic enantioselective perfluorinated 1,3,5-triol synthesis
Among the limited number of methods able to create enantioenriched perfluorinated secondary alcohols,9,10 the aldol reaction seems the most promising given its ability to potentially rapidly assemble elaborated fragments while controlling the hydroxy functionalized stereocenters.11 However, the reported aldolization reactions are unfortunately limited to the generation of simple trifluoromethylated ketols.12 In addition, the most efficient ones are incompatible with perfluorinated aldehyde hydrates thus requiring the application of more elaborated hemiacetals, while suffering from excessive reaction times (4 to 7 days). These slow kinetics constitute a severe limitation for their desired implementation to the proposed more challenging cascade preparation of 1,3,5-triol cores.12d,f,13
To successfully create rapidly perfluorinated 1,3,5-triols, we proposed to take advantage of the high reactivity of 1,3-acetonedicarboxylic acid (2) towards multiple additions.14 Previous aldolizations using this precursor are based on substrate-controlled diastereoselective approaches15 and we set out to identify a suitable catalytic activation mode for the more challenging enantioselective addition to perfluorinated aldehyde hydrate 1a (Table 1).16
Table 1 Identification of a suitable catalytic system for the bi-directional aldolization on perfluorinated aldehyde 1a
Yielda
a Isolated yield.b Determined by 19F NMR and gas chromatography.c Determined by chiral gas chromatography.d Full conversion, yield not determined.e yield, dr and ee within parenthesis are given after purification by recrystallization.f Opposite enantiomer obtained.g Reaction run over 12 hours. The same result is observed using toluene as the solvent.
1 (S,S)-TUC (10 mol%) 38% 1 : 1 2%
2 Quinine (10 mol%) ndd 1 : 1 17%
3 (DHQD)2PHAL (10 mol%) ndd 1 : 1 10%
4 Cu(OTf)2 (10 mol%)/L1-4 (13 mol%) 34–64% 1 : 1 0%
5 Cu(OTf)2 (10 mol%)/L5 (13 mol%) 74% (54%)e 4 : 1 (32 : 1)e 88 (97%)e
6 Cu(OTf)2 (10 mol%)/L6 (13 mol%) 55% 4 : 1 −62%f
7 Cu(OTf)2 (10 mol%) 73% 1 : 1 —
8g L5 (10 mol%) 58% 1 : 1 0%
9 Cu(OTf)2 (10 mol%)/L5 (13 mol%) + 4 Å MS 33% 4 : 1 86%
10 Cu(OTf)2 (10 mol%)/L5 (22 mol%) 59% 4 : 1 88%
Given the behavior of a broad range of organocatalysts in various decarboxylative processes,14b–d we first checked the efficiency of such catalyst structures in our transformation. While it was previously shown that bi-directional aldolization was poorly efficient using organocatalytic activation modes on aliphatic aldehydes,15b the increased electrophilic character of perfluorinated aldehydes facilitated the formation of the ketodiol 4a albeit with poor stereocontrol (entries 1–3). Among all catalysts tested, 10 mol% quinine provided the best 17% ee with a total lack of diastereocontrol (1 : 1 dr) (entry 2). This absence of diastereocontrol indicates that the first generated stereocenter does not control the formation of the second.
The apparent lack of selectivity of most organocatalysts leads us turn our attention to the alternative use of Lewis acids such as chiral copper complexes, initially introduced in decarboxylative aldolizations by the group of Shair.17 Disappointingly, the phosphine containing ligand L1 or different bis-oxazoline (BOX) ligands containing isopropyl, tert-butyl or benzyl substituents (L1–4) were totally unable to control the stereoselectivity of the aldolization forming 4a as a racemate and a 1 : 1 anti-meso mixture (entry 4). In sharp contrast, phenyl substitution in L5 dramatically changed the transition state of the aldolization providing 4a in 4 : 1 dr and 88% ee (entry 5). Of interest, the stereopurity of the ketodiol could be easily improved by purification through simple recrystallization (32 : 1 dr and 97% ee). Finally, increasing the flexibility by removing the gem-dimethyl linker in L6 slightly decreased the selectivity, providing 4a in 62% ee of the opposite enantiomer (entry 6).
This unique enantiocontrol using the simple phenyl substituted BOX ligand L5 is in contrast to previous studies on aldolization17c,d,18 and suggests interactions between the aromatics and the perfluorinated chains during the enantiodetermining step.
In order to further understand this mechanism, several control experiments were also performed. Using Cu(OTf)2 alone, 4a was formed in 1 : 1 dr, indicating that the creation of the second stereocenter does not arise from substrate control but from control by the chiral ligand (entry 7). Using L5 alone as reported by Ma,12f 4a could be formed after prolonged reaction time albeit without any diastereo- or enantiocontrol, confirming the role of the copper complex (entry 8).
Adding 4 Å molecular sieves to the reaction did not change the enantioselectivity (86% ee) while considerably decreasing the yield (33%, Table 1, entry 9). This suggests that the water present does not interfere in the transition state but might considerably help catalyst turn-over possibly through copper complex protonation.
In sharp contrast to the aldolization of aliphatic aldehydes reported by Shair, where excess BOX was responsible for the deprotonation of the pro-nucleophile,17c,d the use of a large excess of the ligand is not necessary to obtain a good efficiency during this transformation (entries 10–11). This is in agreement with the reported reactivity of ketodiacid 2, not requiring any base for its activation by simple Lewis acids.15 In addition, in our process, good levels of enantiocontrol are obtained regardless of the Cu/L* ratio indicating that the kinetics of aldolization by the generated chiral copper complex is much faster than that of the basic BOX ligand or Cu(OTf)2 alone (entries 10–11).19
More surprisingly, determination of the absolute configuration of the ketodiol (vide infra), indicated that the same Cu/L5 combination was inducing an opposite sense of enantioinduction compared to previously disclosed results by Shair on the aldolization using aliphatic aldehydes.17c,d A control experiment performing the reaction on aliphatic aldehyde 5 indicated that the aldol product 6 was formed without any stereocontrol using the same conditions as for perfluorinated aldehyde 1a (Scheme 2(a)).
Scheme 2 Bi-directional aldolization with other aldehydes.
In order to better understand the interactions ongoing in our bi-directional aldolization, we subjected chloral hydrate 7 to the same conditions. Through the use of a Cu(OTf)2/L5 combination, ketodiol 8 was formed in 68% yield, 4 : 1 dr and 90% ee (Scheme 2(b)). Of importance, this hexachlorinated ketodiol 8 has the structure of a natural product that might explain the observed toxicity of oxytropis common feed plants.20 The corresponding racemic molecule has already been prepared and further derivatized through desymmetrization, highlighting the synthetic potential of this enantioselective preparation of 8.21
Altogether, these results suggest that the present process is mechanistically distinct from previous Cu/BOX-catalyzed decarboxylative aldolizations with non-fluorinated aliphatic aldehydes, pointing out a crucial role of the aromatic substituent of the ligand.
A catalytic cycle for the bi-directional aldolization taking into account all these observations is depicted in Scheme 3. From the carboxylic acid coordinated chiral complex A, deprotonation provides the reactive enolate B. As demonstrated previously, the aldolization event creating the new stereocenter precedes the decarboxylation.15c,17d With this experimental evidence, a potential preferred transition state accounting for the unique stereocontrol is presented in Scheme 3b(1). The crucial interaction governing the enantiodiscrimination might arise from F–π aromatic repulsion disfavoring transition state (2). This is further confirmed by the excellent result obtained using chloral 7 and eliminates a discrimination through less conventional F–π aromatic attractive interactions.22 In addition to additional interactions, the better results obtained with halogenated aldehydes vs. aliphatic ones might also originate from their higher electrophilicity. This might favor a faster nucleophilic addition prior to competing ligand exchange between the ketodiacid and the chiral ligand.15b From the resulting enolate C, ligand exchange followed by the second catalyst controlled aldolization-decarboxylation provides the new enolate E. The control of the second aldolization event by the chiral ligand is responsible for an overall increase in the enantiomeric excess on the product at the expense of diastereoselectivity through an amplification of chirality.23 At this stage, enolate protonation potentially assisted by the water coming from the aldehyde hydrate source provides ketoalcoholate F. Final ligand exchange with a new molecule of ketodiacid 2 liberates the enantioenriched product and regenerates the active catalytic species A.
Scheme 3 Proposed catalytic cycle and postulated transition state.
With the optimized conditions in hand, different ketodiols 4a–c possessing perfluorinated chains of different lengths were prepared through the bi-directional cascade (Scheme 4). Reaction conditions tolerated the insertion of perfluorinated chains of C1 (4c), C3 (4a) or C4 (4b) length. In addition, in all cases the ketodiols were generated in good yields (54–71% yield) and good to excellent diastereo- and enantiocontrols (11.5 : 1 to 32 : 1 dr and 96–97% ee). Of particular interest, the developed conditions are amenable to scale up (25 mmol of starting 1) without tedious column chromatography requirement while tolerating the presence of water arising from the use of the commercial hydrate forms of the perfluorinated aldehydes.
Scheme 4 Scope of the copper-catalyzed enantioselective aldolization with perfluorinated aldehydes.
In addition to the bi-directional reaction, we also tested the present conditions with different 1,3-ketoacids 9. Insertion of linear alkyl chain (10), aromatic (11) or tert-butyl groups (12–14) provided the 1,3-ketols in 76 to 96% ee. It must be pointed out that using the chiral copper complex, much higher reaction TOF is observed as compared to previous studies.12d,f Indeed, full conversion is obtained after only a few hours vs. 4–7 days for previous studies, a strong improvement leaving room for optimization of the conditions to better adjust the results to the different ketoacid structures. Finally, single crystal X-ray diffraction of 14 confirmed the absolute configuration of the obtained products.24
With a convenient method to directly access the desired enantioenriched ketodiols, simple sodium borohydride reduction provided the three different perfluorinated 1,3,5-triols 3a–c with different lateral chain lengths (Scheme 5). Of interest, all three triols were crystalline, allowing the preparation of these crucial compounds in good yield and nearly perfect stereocontrol (11.5 : 1 to 30 : 1 dr and >96% ee) by simple recrystallization. Single crystal X-ray diffraction of triol 3c also further confirmed the absolute configuration.24 Of importance, in the crystal assembly, the molecular packing is stabilized through several fluorine atoms acting as hydrogen bond acceptors, adding new evidence to the long debate on the existence of such interactions.25
Scheme 5 Reduction of the ketodiols and single crystal X-ray diffraction of 3c.
Perfluorinated 1,3,5-triols, new tools for selective supramolecular recognition
As mentioned in the introduction, host molecules able to recognize different guests through supramolecular interactions are crucial for a wide array of applications. Most notably, anion coordination is central for sensing, extraction, catalysis, smart materials and discovery of innovative therapies.26 In this context, identifying new non-charged molecules for anion coordination is of crucial importance. For this purpose, we initially tested the anion binding properties of the three triols in CD3CN to the biologically relevant chloride anion through 1H NMR monitoring using Thodarsson method (Table 2).27
Table 2 Anion binding properties of perfluorinated 1,3,5-triols in CD3CNa
a The addition of X− to the polyols resulted in large downfield shifts of the hydroxyl hydrogens. Association constants from triplicate experiments were obtained by fitting these spectroscopic data to 1 : 1 binding isotherm models, using the Thordarson method.
K (Cl−) 25 °C 2100 M−1 3750 M−1 4400 M−1
K (S)-15 nd 8100 M−1 nd
K (R)-15 nd 1790 M−1 nd
K (S)-15/K (R)-15 nd 4.5 nd
All three triols provided remarkable chloride binding ability for such poorly preorganized acyclic non-charged hosts, with 1 : 1 host : guest coordination constants ranging from 2100 to 4400 M−1. Most notably, the association constant did not follow a linear behavior depending on the length of the fluorinated chain, indicating that the electron-withdrawing character of the side chain is not the single responsible factor for the enhanced binding. Indeed, while the C1 (3c) and C4 (3b) perfluorinated chains provided the higher constants, the C3 (3a) chain gave lower binding.
With the excellent behavior of all three triols on the model chloride anion, we next turned our attention to the more challenging coordination to chiral anions. A molecule's ability to selectively recognize one enantiomer of a chiral guest is fundamental for many important biological processes, as different enantiomers often possess totally different biological profiles but is also of importance for catalysis.28
For this purpose, we choose to study 3b, possessing one of the best binding constants and the longer perfluorinated chain for potential interactions, to test fluorinated triols' ability in chiral recognition of the model binol-phosphate derived anion 15.29 Of utmost importance, this triol was able to selectively recognize both enantiomers of the phosphate 15, providing a K(S)/K(R) of 4.5, among the highest observed for such an anion.5,6 This clearly demonstrates for the first time the efficiency of acyclic polyol scaffolds as a platform for chiral recognition. In addition, the anion binding constant with the major enantiomer is high (8100 M−1), which is a crucial parameter for further application of the synthesized triols to other technologies.
Identifying new scaffolds and concomitantly discovering new synthetic strategies to directly access them represents a step forward highlighting the maturity of organic chemistry. In this manuscript, we have demonstrated that chiral perfluorinated triols could be efficiently prepared diastereo- and enantio-selectively through copper-catalyzed bi-directional decarboxylative aldolization followed by reduction. The use of a phenyl substituted bis-oxazoline ligand provides unique enantiocontrol through crucial aromatic–fluorine interactions. The reaction occurs rapidly under mild conditions and tolerates the presence of water. Furthermore, the reaction could be extended to the preparation of naturally occurring hexachlorinated ketodiol of great synthetic utility.
In addition, we have shown that the obtained perfluorinated 1,3,5-triols possess enhanced recognition ability. The strength of the central triol framework ensures excellent anion binding properties while the key molecules demonstrate the selective chiral anion recognition ability of synthetic 1,3-polyols.
The present study opens broad perspectives for the preparation of chiral fluorinated scaffolds. In addition, it also broadens the possibilities offered by alcohol coordination with strong implications ranging from biology to materials or catalysis.
The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.
A patent on the preparation and properties of perfluorinated 1,3,5-triols has been submitted by Céline Sperandio, Jean Rodriguez and Adrien Quintard. Patent declaration. EP19 305862.5. Submitted 27 June 2019.
The Centre National de la Recherche Scientifique (CNRS) and the Aix-Marseille Université are warmly acknowledged for financial support. All technical staff from Aix-Marseille Spectropole are acknowledged for their support.
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For efficient enantioselective cascade aldolizations controlling multiple alcohol stereocenters: (a) K. Mikami, S. Matsukawa, M. Nagashima, H. Funabashi and H. Morishima, Tetrahedron Lett., 1997, 38, 579 CrossRef CAS; (b) D. B. Ramachary, R. Mondal and R. Madhavachary, Org. Biomol. Chem., 2012, 10, 5094 RSC; (c) Y. Shimoda, T. Kubo, M. Sugiura, S. Kotani and M. Nakajima, Angew. Chem., Int. Ed., 2013, 52, 3461 CrossRef CAS PubMed; (d) G. Valero, J. M. Ribo and A. Moyano, Chem. – Eur. J., 2014, 20, 17395 CrossRef CAS PubMed; (e) L. Lin, K. Yamamoto, H. Mitsunuma, Y. Kanzaki, S. Matsunaga and M. Kanai, J. Am. Chem. Soc., 2015, 137, 15418 CrossRef CAS PubMed; (f) S. Kotani, K. Kai, Y. Shimoda, H. Hu, S. Gao, M. Sugiura, M. Ogasawara and M. Nakajima, Chem. – Asian J., 2016, 11, 376 CrossRef CAS PubMed; (g) S. Kotani, K. Kai, M. Sugiura and M. Nakajima, Org. Lett., 2017, 19, 3672 CrossRef CAS PubMed; (h) A. Quintard and J. Rodriguez, Org. Lett., 2019, 21, 453 CrossRef CAS PubMed.
This molecule derived in the kg scale from citric acid was initially used by Robinson in his famous tropinone synthesis: (a) R. Robinson, J. Chem. Soc., Trans., 1917, 111, 762 RSC. For reviews on decarboxylative aldolization reactions, see: (b) Y. Pan and C.-H. Tan, Synthesis, 2011, 13, 2044 Search PubMed; (c) Z. L. Wang, Adv. Synth. Catal., 2013, 355, 2745 CrossRef CAS; (d) S. Nakamura, Org. Biomol. Chem., 2014, 12, 394 RSC.
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See the ESI† for the complete catalyst and ligand optimization.
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Cu(OTf)2 and L5 must be stirred for 30 minutes at least to generate the active chiral catalyst. If the substrates are added earlier, competing coordination of the ketodiacid 2 to the copper complex (see ref. 15b) generates an achiral reactive complex thus forming 3a in lower enantiocontrol. The use of more electrophilic perfluorinated aldehydes as compared to aliphatic aldehydes might also favor rapid aldolization, avoiding this undesired slower competitive ligand decoordination process.
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† Electronic supplementary information (ESI) available. CCDC 1939200 and 1939261. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc05196a
This journal is © The Royal Society of Chemistry 2020

redpajama_set_name: RedPajamaCommonCrawl


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100 bison find a new home on the Wolakota Buffalo Range
Video courtesy of WWF
MISSION, S.D. — On Friday, 100 bison found a new home on the Wolakota Buffalo Range on the land of the Sicangu Oyate, commonly known as the Rosebud-Sioux Tribe.
The bison are the first of as many as 1,500 animals to set foot on the 28,000 acres of native grassland. This is considered the beginning of what will become North America's largest Native-owned and managed bison herd.
Photo courtesy of WWF/Clay Bolt
The project is being advanced by a partnership between the Rosebud Economic Development Corporation (REDCO) and WWF with support from Tribal Land Enterprise, the Rosebud Sioux Tribes' land management corporation, and the U.S. Department of the Interior.
The Sicangu Oyate are revitalizing their relationship with bison to demonstrate the potential this creates for economic, ecological, and cultural resiliency, despite what's happening in the world now like the pandemic and social unrest.
WWF Bison 1
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"The sacred relationship between Native nation communities and the buffalo is part of a shared story of strength, resilience and economic revitalization," said Wizipan Little Elk, CEO, REDCO. "The arrival of the buffalo marks a new beginning for the Sicangu Oyate, where cultural, ecological, and economic priorities are equally celebrated and supported and are of great benefit to our community and serve as an example to the entire world."
The WWF has invested more than $2.2 million over the past five years in bison restoration efforts with indigenous communities in the Northern Great Plains.
Additional bison will be delivered over the next five years as part of the U.S. Department of the Interior's 2020 Bison Conservation Initiative, a 10-year plan announced in May.
"Today marks a long-overdue homecoming for these iconic animals," said Carter Roberts, WWF president and CEO. "And it represents a reunion with the communities who lived with them for millennia in a symbiotic relationship—and who can now do so again. WWF was honored to partner with the Rosebud Economic Development Corporation and the U.S. Department of the Interior to help make this day possible."
Categories: ConnectCenter1-Culture and Art, South Dakota News
Tags: bison, Carter Roberts, REDCO, Rosebud Sioux Tribe, Sicangu Oyate, Wizipan Little Elk, Wolakota Buffalo Range, WWF
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Senior men can find themselves managing a kitchen and preparing food. Finding and learning to use kitchen tools can be a challenge and so can learning to store food. These are all things that elderly women have been doing for decades and now the men must learn.
Sometimes, the Senior caregiver prepares food perfectly for an ill spouse or loved one but does not eat properly him or herself. It's important to feed your body properly.
Leftovers can be the hardest to put away so that they are edible when we want to eat them. We all like variety in our diet so leftovers can stay in the refrigerator, freezer or cupboard for awhile before we consider them again. Sometimes they get pushed to the back and forgotten.
Some people purchase food in large quantities because there is a bargain price or the items are seasonal or not readily available. Good and safe storage techniques insure good flavor later on.
If it smells bad, it probably is!


text:
Why It's Time for Evidence Documentation Methods to Receive an Update
Crime scene documentation and evidence documentation is nothing new within the criminal justice system. Since the late 19th century, investigators across the globe have implemented crime scene photography to preserve evidence. Photography revolutionized evidence and crime scene preservation, which were, and still are, accompanied by sketches and physical evidence.
Over a century has passed since then, and technology has advanced rapidly. Many methods of crime scene documentation have not.
Everyday citizens can use the latest iPhone model to instantly share, stream, and spread information. Meanwhile, law enforcement agencies and prosecutors rely on physical methods of evidence documentation. This could include the means of USB drives, CDs, and printed documents.
If your average person can easily share photos and memes through cloud software, why don't police officers and prosecutors have access to these same technologies that are reflective of the 21st century?
As the public demands increased transparency from prosecutors and law enforcement agencies alike, it is more crucial than ever that evidence is preserved as accurately as possible. Through updated technology, law enforcement agencies and prosecutors can more efficiently organize information and effectively streamline documentation.
Why Digital PCMS?
Why use digital and integrated evidence documentation software (versus physical documentation)? Law enforcement officials often must enter digital evidence into multiple systems since their existing software and processes are not integrated. Legacy technology and evidence management often do not keep all evidence organized within the same, searchable database. Digital, Integrated Evidence Documentation Software saves law enforcement agencies' and prosecutors' valuable time and allows them to focus on the most important, pressing tasks at hand, such as protecting their local communities.
Now, let's examine some common methods of crime scene documentation while comparing older and newer approaches.
What is a Record Management System (RMS) or Prosecutor Case Management System (PCMS)?
The Necessity of Digital RMS for Law Enforcement Agencies
National Incident-Based Reporting System (NIBRS) Compliance
The Necessity of Digital PCMS for Prosecutors
Additional Advanced Features of PCMSs
Digital Evidence Documentation vs. Physical
What is a Record Management System or Prosecutor Case Management System?
As described above, many prosecution teams and law enforcement agencies still rely on outdated, physical crime scene documentation methods, such as physical binders and manila folders—not to mention the USB drives and CDs we've already listed. Not only are these methods tedious, but they are also easily misplaced, disorganized, and require physical transportation. Printing and transporting these documents also contribute to added costs and time.
Law enforcement agencies and prosecutors alike can use digital systems to electronically organize files, documents, and pertinent information. Compared to physical files and information, digital Record Management Systems (RMS) and Prosecutor Case Management Systems (PCMS) provide the potential to share information across jurisdictions, from agency to agency, and even across continents. This is crucial in providing full-scope, accurate information and in the past has been a dangerous barrier.
Now, let's better understand the different functionalities of RMSs and PCMSs.
As we briefly described above, it is vital that law enforcement agencies share information across jurisdictions.
As stated in an article from Police1, "Perpetrators don't care about county or city lines when they commit crimes."
Without updated and digital RMS, law enforcement agencies lack access to vital information that could potentially save the lives of both citizens and officers.
The U.S. Department of Justice describes that "Calls for service records and investigative, arrest, criminal identification, detention, and even civil records hold information that by themselves mean little; however when pieced together with information from other jurisdictions, the result can help with all levels of investigations and aid in safeguarding the Nation."
RMS, such as CivicRMS, allow for outcomes such as increasing apprehension (the arrest, capture, or taking into custody of a person) rates and reduced victimization through proactivity, among numerous other benefits.
As law enforcement agencies move toward NIBRS compliance, RMSs must provide NIBRS-compliant reporting. According to the Bureau of Justice Statistics, NIBRS was created to better measure and estimate crime at the federal level by capturing detailed data about the characteristics of criminal incidents including a broad array of offenses; types and amount of property lost; demographic information about victims, offenders, and persons arrested; and what type of weapon, if any, was used in the incident.
Some other key aspects of NIBRS include the ability to use standardized data to compare crime across jurisdictions and for strategic analysis at various levels (such as local, state, and national). Additionally, NIBRS creates profiles of victims, offers insight into accidents involving multiple offenses, and collects data on 52 crimes across 24 offense categories.
An RMS, such as CivicRMS, helps streamline reporting, which maximizes officers' time on patrol. Alongside NIBRS compliance, CivicRMS maintains reporting compliance with other local, state, and federal organizations. Additionally, CivicRMS allows users to search hundreds of millions of records in less than a second.
To learn more about CivicRMS, check out our previous blogs on 4 Features to Look for When Shopping for Police Technology, Why Technology is Becoming Crucial in Law Enforcement, and 5 Reasons to Combine CAD with a Quality RMS.
PCMSs optimize, organize, and track a prosecutor's work throughout the entirety of the prosecution process.
In an article from SEARCH, the National District Attorneys Association (NDAA) explains that "An ideal PCMS…efficiently streamlines a prosecutor office's capability to collect, store, retrieve, edit, archive, and view information, records, documents, or files required of prosecutors to fulfill their responsibilities. Additionally, it may support the automated exchange of data with justice partner agencies to support investigations or prosecutions."
Used by prosecutors, solicitor generals, and state attorneys, PCMS, like CivicCase, facilitates quicker case handling through storage, management, and distribution of all assets connected to a case. Police depend on prosecutors almost as much as prosecutors depend on them. The integration of police records management systems with prosecution case management shares data seamlessly, reducing duplicate data and improving agency efficiency when staff can feel overworked with administrative tasks. When prosecution and law enforcement spend time sending cases back for further investigation or piecing together further case-related documents in an outdated fashion, the impact is a slowed response to general public safety.
Case management, when combined with document management like CivicDocs, helps to preserve the document visibility from discovery and better tracks and shares the digital files, lightening the load of the previously mentioned manila folders and banker boxes that prosecutors would bring to and from the courtroom.
This type of evidence documentation software, like CivicEye's CivicDocs, centralizes documents into a searchable, streamlined database. These digital files, unlike their physical counterparts, cannot be misplaced and can be instantly shared from the prosecutor to the defense team. Additionally, users can instantly upload batch files while still maintaining the original file material. CivicDocs also allows users to easily edit the viewership of certain docs to maintain confidentiality.
Audit Logs and Document Review Software for Electronic Evidence
With outdated, physical materials, it can be easy to dispute which parties have/have not had access to specific information, files, and documents. CivicDocs's document review software for electronic evidence issues accurate audit logs that document who has accessed specific files, how often, and at what time and location (through their IP address). The audit log also lists which files have been printed and/or saved by who and where. Document verification tools provide processes that show if files have been manipulated.
Sharing Discovery Between Defense Attorneys and Prosecutors
The discovery process is a legal process that largely focuses on the exchange of data and case information between parties to a case. These parties "disclose relevant information about the case to each other and must include all information that is not otherwise 'non-discoverable'" (NDAA).
During the discovery process, prosecutors must provide all information or evidence they intend to use against a defendant during trial. This information could include crime scene evidence, witness statements, law enforcement statements, defendant statements, police reports, disclosures, and more. Additionally, the discovery is required to include all exculpatory evidence (evidence, such as a statement, that is favorable to the defendant and tends to excuse, justify, or absolve the alleged fault or guilt of a defendant).
Prosecutors and defense teams can dispute when and how they received specific documentation, but evidence documentation software easily allows users to share information, even with those outside of the software's subscription. Prosecutors and defense teams alike can upload their files quickly and efficiently, adhering to all required aspects of the discovery process.
CivicCase, CivicEye's advanced end-to-end legal case management software, allows each party to access forms and information through a custom portal. This allows individuals to complete their personal tasks and expedite the case's progression. The software translates complex forms into interactive ones, and virtually any paper or electronic form can integrate into the system. Additionally, the software features flexible form validation, interactive content elements, and pixel-perfect form rendering to match originals. Like CivicRMS and CivicDocs, CivicCase operates through a secure cloud network, which means it is accessible anywhere and at any time.
Preserving Chain-of-Evidence
Like other important files and documents, updated crime scene technology can better preserve chain of evidence—a process and record that shows who obtained the evidence; where and when the evidence was obtained; who secured the evidence; and who had control or possession of the evidence.
Prosecutors, law enforcement agencies, and criminal justice agencies work together to manage evidence, and in certain scenarios, prosecutors must maintain control of evidence. CivicDocs's features provide accurate audit logs (as described above) and clearly document the trail of data exchange.
Modern software like CivicDocs is not only secure but also can help keep your work within both state and federal compliance. Alongside CivicDocs, CivicCase works to provide other case management features such as digital form creation, that integrates virtually any paper or electronic form into the system, allows for flexible form validation, includes interactive content elements, and provides pixel-perfect form rendering to match originals.
How To Integrate Evidence Documentation Software Seamlessly into Your Current Work
CivicEye's digital system of evidence documentation, PCMS, and RMS can easily integrate with one another. This makes the transfer of data both easy and secure. Additionally, CivicEye offers 24/7, 365 support, alongside other helpful training to acclimatize new users.
Contact us today if you would like to learn more about CivicEye's products and how they can revolutionize your public safety agency.
To learn more about CivicRMS, CivicDocs, and/or CivicCase and schedule a demo, click here.
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