Unusual Deoxidative Coupling Reaction of β-Sulfinyl Esters with Benzylic Trimethylammonium Salts.

J Org Chem

State Key Laboratory of Geohazard Prevention and Geoenvironment Protection, College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, China.

Published: June 2021

A KOH-promoted unusual deoxidative coupling reaction of β-sulfinyl esters with benzylic trimethylammonium salts to produce thioethers is discovered for the first time. If quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantiomerically enriched benzyl thioethers (>95-99% ee) with configurations opposite to those of the enantiomerically enriched amines are obtained.

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Source
http://dx.doi.org/10.1021/acs.joc.1c00615DOI Listing

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