Authors: Huw M. L. Davies and Qihui Jin
Proc. Nat. Acad. Sci.,
2004, 101, 15, 5472-5475
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.