Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy

Author:

Werner Erik W.1,Mei Tian-Sheng1,Burckle Alexander J.1,Sigman Matthew S.1

Affiliation:

1. Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112, USA.

Abstract

From C=C to C=O The palladium-catalyzed Heck reaction is widely used to form carbon-carbon bonds between aryl rings and olefins, after which elimination of a hydrogen atom restores the olefin's double bond. Werner et al. (p. 1455 ; see the Perspective by Gilbertson ) present a variant of this reaction in which a hydrogen atom is instead lost from an alcohol center elsewhere in the molecule, yielding a ketone and a chiral center where the arene is bound. The process is highly enantioselective and also versatile: The alcohol can be sited one, two, or even three carbons away from the olefin.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

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