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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 14
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Original Articles

Regio- and Diastereoselectivity in the Thiomethylation of α-(1-Hydroxyalkyl)acrylate Derivatives

Philip O. Deane Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
,
Jeffry J. Guthrie-Strachan Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
,
Perry T. Kaye Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
&
Ruth E. Whittaker Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
Pages 2601-2611 | Received 26 Nov 1997, Published online: 20 Aug 2006
 
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Abstract

The regio-and diastereoselectivity of reactions of selected α-(1-hydroxyalkyl)acrylate derivatives with sodium methanethiolate have been investigated. The hydroxy compounds typically undergo conjugate addition with up to 66% d.e., while the acetoxy and bromo analogues favour SN' and SN reactions, respectively.

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