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The asymmetric synthesis of allylic alcohols using a recoverable chiral sulphoxide

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
11
Identifiers
DOI: 10.1016/0040-4039(94)88346-7

Abstract

Abstract The enantiomerically pure cyclic sulphinamide S (S)R-(+)- 3 reacts with the sodium enolates of ketones to give the corresponding homochiral sulphoxides. Reduction of the carbonyl group in these products using DIBAL-H or DIBAL-H/ZnBr 2 gives complementary products of high diastereoisomeric excess. This methodology has been applied to the synthesis of an allylic alcohols in high enantiomeric excess.

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