Cycloaddition Reactions in Organic Synthesis
Published on 28. September 1990
Book
Paperback/Softback
384 pages
978-0-08-034712-7 (ISBN)
Description
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.
More details
Series
Language
English
Place of publication
Amsterdam
Netherlands
Publishing group
Elsevier Science & Technology
Target group
College/higher education
Professional and scholarly
Illustrations
600ill.
Dimensions
Height: 248 mm
Width: 171 mm
Weight
703 gr
ISBN-13
978-0-08-034712-7 (9780080347127)
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Schweitzer Classification
Content
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.