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Paper text:
the general procedure for the one - pot dcc reaction as described in figure 2 is as follows .
pt(dba)3 ( 1.0 mol % ) , ( r , r)-l1 ( 1.2 mol % ) , b2(pin)2 ( 1.05 equiv . ) , and anhydrous thf ( [ substrate ] = 1.0 m ) are stirred together at 80 c for 15 minutes .
is added and the reaction mixture is stirred at 60 c for 3 hours . upon cooling to ambient temperature , pd(oac)2 ( 1.0 mol % ) , followed by ruphos ( 1.0 mol % ) , the electrophile ( 1.5 equiv . ) , koh ( 3.0 equiv . ) , additional thf and deoxygenated water ( [ substrate ] = 0.1 m ; 10:1 v : v thf : h2o ) are added and the reaction mixture is heated to 70 c for 12 hours . the reaction is then cooled to 0 c and treated with 3 m aqueous naoh and 30% h2o2 . after 4 hours at ambient temperature , excess h2o2
the resulting material is purified by flash chromatography on silica gel . for complete experimental details and characterization of all new compounds ,
amongst prospective starting materials for organic synthesis , terminal ( monosubstituted ) alkenes are ideal . in the form of -olefins , they are manufactured on enormous scale and they are the core product features from many organic chemical reactions . while their latent reactivity can easily enable hydrocarbon chain extension , alkenes also have the attractive feature of being stable in the presence of many acids , bases , oxidants and reductants . in spite of these impressive attributes , relatively few catalytic enantioselective transformations 
 have been developed that transform aliphatic -olefins in > 90% ee and , with the exception of site - controlled isotactic polymerization of -olefins,1 none of these processes result in chain - extending c - c bond formation to the terminal carbon.2 , 3 , 4 , 5 , 6 herein , we describe a strategy that directly addresses this gap in synthetic methodology and present a single - flask catalytic enantioselective conversion of terminal alkenes into a range of chiral products . 
 these reactions are enabled by an unusual neighboring group participation effect that accelerates pd - catalyzed cross - coupling of 1,2-bis(boronates ) relative to nonfunctionalized alkyl boronate analogs . in tandem with enantioselective diboration 
 , this reactivity feature connects abundant alkene starting materials to a diverse array of chiral products . importantly with respect to synthesis utility , 
 the tandem diboration / cross - coupling reaction ( dcc reaction ) generally provides products in high yield and high selectivity ( > 95:5 enantiomer ratio ) , employs low loadings ( 12 mol % ) of commercially available catalysts and reagents , it offers an expansive substrate scope , and can address a broad range of alcohol and amine synthesis targets , many of which can not be easily addressed with current technology .