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Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement.

ABSTRACT: 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.

SUBMITTER: Davies HM

PROVIDER: S-EPMC397407 | biostudies-literature | 2004 Apr

REPOSITORIES: biostudies-literature

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Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement.

Davies Huw M L HM Jin Qihui Q

Proceedings of the National Academy of Sciences of the United States of America 20040315 15

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 ei ...[more]

PMID: 15024094

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