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 | CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, 8
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By
W. Carruthers, University of Exeter, Exeter, UK
Included in series
Tetrahedron Organic Chemistry,
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.
Audience
For advanced undergraduate and graduate chemistry students, and organic research chemists involved in synthesis in academic and industrial research.
Contents
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.
| Bibliographic details |
Hardbound, 0 pages, publication date: OCT-1990
ISBN-13: 978-0-08-034713-4
ISBN-10: 0-08-034713-4
Imprint: PERGAMON
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| Price and Ordering |
Price:
USD 153 EUR 108.95 GBP 92.99
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Last update: 29 Oct 2009
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