Catalytic Enantioselective Negishi Reactions of Racemic Secondary Benzylic Halides

Forrest O. Arp and Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2005, 127 (30), pp 10482–10483
DOI: 10.1021/ja053751f
Publication Date (Web): July 8, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, gcf@mit.edu

Abstract

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This report describes the first enantioselective cross-couplings of racemic secondary benzylic halides, specifically, nickel-catalyzed Negishi reactions of bromides and chlorides. The catalyst components are commercially available and air-stable, and the reaction is not highly oxygen- or moisture-sensitive (it can be set up in the air). The method has been applied to the catalytic enantioselective synthesis of intermediates employed by others in the generation of bioactive compounds (e.g., trikentrin A and an androgen receptor agonist).

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History

  • Published In Issue August 03, 2005
  • Received June 8, 2005

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