Synlett 2007(3): 0435-0438  
DOI: 10.1055/s-2007-967945
LETTER
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Kinetic Resolution of 1,3-Cyclohexadiene Monoepoxide with Grignard Reagents

Renaud Millet, Alexandre Alexakis*
Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva, Switzerland
Fax: +41(22)3793215; e-Mail: alexandre.alexakis@chiorg.unige.ch;
Further Information

Publication History

Received 24 November 2006
Publication Date:
07 February 2007 (online)

Abstract

Chiral ferrocenyl-based diphosphines lead to kinetic ­resolution of 1,3-cyclohexadiene monoepoxide with moderate to good enantioselectivity (up to 90% ee) and good regioselectivity with various Grignard reagents through an anti-SN2′ pathway.