Catalytic Asymmetric Reactions for Organic Synthesis: The Combined C-H Activation/Cope Rearrangement

The development of new catalytic asymmetric reactions can lead to exciting new strategies for organic synthesis. This article describes the synthetic utility of the combined C-H activation/Cope rearrangement, achieved by dirhodium tetraprolinate-catalyzed reaction of vinyldiazoacetates with compound...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 2004-04, Vol.101 (15), p.5472-5475
Main Authors: Huw M. L. Davies, Jin, Qihui, Halpern, Jack
Format: Article
Language:English
Subjects:
Alkenes
Asymmetric Catalysis Special Feature Part I
Catalysis
Cycloaddition
Esters
Molecular biology
Organic chemistry
Physical Sciences
Solvents
Stereochemistry
Synthetic chemistry techniques
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Summary:The development of new catalytic asymmetric reactions can lead to exciting new strategies for organic synthesis. This article describes the synthetic utility of the combined C-H activation/Cope rearrangement, achieved by dirhodium tetraprolinate-catalyzed reaction of vinyldiazoacetates with compounds containing allylic C-H bonds. The transformation is highly diastereoselective and enantioselective. The product distribution, however, is highly substrate dependent, the major side products being either direct C-H activation or cyclopropanation.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0307556101