☆ 4.8 Article

Convenient Synthesis of Allylic Thioethers from Phosphorothioate Esters and Alcohols

ORGANIC LETTERS (2010)

Journal

ORGANIC LETTERS

Volume 12, Issue 11, Pages 2668-2671

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol1009202

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Categories

Chemistry, Organic

Funding

Dartmouth College
Walter and Constance Burke Foundation

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Abstract

The synthesis of allylic thioethers arising from the reaction between phosphorothioate esters and alcohols is described. The synthesis is accomplished in one step by the addition of an exogenous alkoxide to the corresponding allylic phosphorothioate ester. It is demonstrated that this process is amenable to various functional groups and a wide variety of heterocycles. In contrast to conventional methods for thioether synthesis, no malodorous sulfur compounds such as thioacetic acid or thiols are required.

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