J. Am. Chem. Soc., 126 (46), 15038 -15039, 2004. 10.1021/ja0454485 S0002-7863(04)05448-4
Web Release Date: October 28, 2004

Copyright © 2004 American Chemical Society

Lewis Acid-Mediated Selective Chlorinations of Silyl Enolate

Yanhua Zhang, Kazutaka Shibatomi, and Hisashi Yamamoto*

Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637

yamamoto@uchicago.edu

Received July 28, 2004

Abstract:

A new method involving efficient, widely applicable, and highly selective -chlorination of simple silyl enolate with Lewis acid and an ,-dichloro-1,3-dicarbonyl controller unit was reported. Diastereoselectivity and enantioselectivity of the reaction were investigated. High reactivity and selectivity were achieved by using ,-dichlorinated malonic ester.


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