Enantioselective Deprotonation of 2,6-Disubstituted Cyclohexanones with a Homochiral Magnesium Amide Base and the Observation of a Novel Kinetic Resolution Process

Kenneth W. Henderson; William J. Kerr; Jennifer H. Moir

doi:10.1055/s-2001-16048

Synlett 2001; 2001(8): 1253-1256
DOI: 10.1055/s-2001-16048

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Enantioselective Deprotonation of 2,6-Disubstituted Cyclohexanones with a Homochiral Magnesium Amide Base and the Observation of a Novel Kinetic Resolution Process

Kenneth W. Henderson^* , William J. Kerr, Jennifer H. Moir

^*Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, Scotland, UK; Fax + 44 141 548 42 46; E-mail: w.kerr@strath.ac.uk

Abstract

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A recently developed homochiral magnesium amide base has been shown to be highly effective in the asymmetric deprotonation of cis-2,6-disubstituted cyclohexanones, affording excellent levels of both conversion and enantioselection (up to > 99.5 : 0.5 e.r.). In addition, a novel kinetic resolution process has been realised with the corresponding trans-disubstituted substrates, allowing access to optically enriched enol ethers and chiral ketones.

asymmetric synthesis - enantioselective deprotonation - kinetic resolution - magnesium

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