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