Demonstrates the wide scope of cycloaddition reactions, including the Diels-Alder reaction, the ene reaction, 1,3-dipolar cycloadditions and [2+2] cycloadditions in organic synthesis. The author, a leading exponent of the subject, illustrates the ways in which they can be employed in the synthesis of a wide range of carbocyclic and heterocyclic compounds, including a variety of natural products of various types. Special attention is given to intramolecular reactions, which often provide a rapid and efficient route to polycyclic compounds, and to the stereochemistry of the reactions, including recent and developing work on enantioselective synthesis.
For advanced undergraduate and graduate chemistry students, and organic research chemists involved in synthesis in academic and industrial research.
Cycloaddition Reactions in Organic Synthesis, 1st Edition
Section headings and selected subheadings: The Diels-Alder Reaction - General Aspects.
The dienophile. Hetero-dienophiles - aldehydes, thiocarbonyl compounds, N-sulphinylsulphonamides, imines, nitroso compounds. The diene. ortho
-Quinodimethanes. Heterodienes. Reactions in water. Reactions under high pressure. Catalysis by Lewis acids. Regiochemistry. Stereochemistry. Asymmetric reactions. Retro reactions. Intermolecular Diels-Alder Reactions.
Stereoselectivity. Hetero-substituted dienes and dienophiles. With alkoxy- and silyloxy-dienes. alphabeta-Unsaturated aldehydes as dienes. Imines as dienophiles. Nitroso compounds as dienophiles-synthesis of 4-amino-alcohols. N-Sulphinylsulphonamides-synthesis of vicinal amino-alcohols. Synthesis of benzene derivatives. Synthesis of quinones. Retro reactions. Intramolecular Diels-Alder Reactions.
Stereoselectivity. Diastereoselection. Synthesis of terpenoids. Synthesis of alkaloids. Nitroso compounds. Miscellaneous [4+2] Cycloadditions.
Allyl anions and allyl cations. Oxyallyl cations. Pentadienyl cations. Cycloadditions with trimethylenemethane. meta
-Photocycloaddition to benzene derivatives. Cobalt-catalysed trimerisation of acetylenes. [4+4] cycloaddition of 1,3-dienes. The Ene Reaction.
Hetero-ene reactions. Intramolecular ene reactions. Diastereoselection. Magnesio-ene reaction. 1,3-Dipolar Cycloaddition Reactions.
Stereoselectivity. Azomethine ylides. Nitrile oxides. Azides, azomethine imines and diazoalkanes. [2+2] Cycloaddition Reactions.
Ketenes. Ketene-imminium salts. Photocycloaddition to enones. De Mayo reaction. Copper-catalysed photocycloaddition of hepta-1,6-dienols. Paterno-Buchi reaction. Index.
Quotes and reviews
@qu:This is an excellent explanatory book that looks at a structure building relationship of general use in organic chemistry. The book stylishly written and edited and will undoubtedly be of value to all those with an interest in this area of organic chemistry.
@source:Chemistry in Britain
@from:Herbert Waldmann, Institut für Organische Chemie, Germany
@qu:Carruther's book succeeds well in its aims. It contains a wealth of elegant and well-chosen examples, which are very well-suited for illustrating lectures to advanced students. At the same time it provides the interested synthetic chemist, whether in a university of industry, with an excellent overview of the current state of research (up to 1988). Thus the monograph fits well into the scheme of the other volumes in this "Organic Chemistry" series. Since no other comparable work exists at present, and this volume is also very attractively priced, its purchase can be recommended unreservedly.
@from:D W Knight
@qu:...it provides an excellent introduction to cycloaddition reactions as well as the useful literature leads and it therefore should be readily available to all Postgraduate students working in synthetic organic chemistry.
@source:Journal of Chemical Technology & Biotechnology