Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Paul MacLellan, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

31 Citations (Scopus)

Abstract

Lithiation of N-aryl S-α-alkylbenzyl thiocarbamates leads to rearrangement with migration of the N-aryl ring to the anionic centre α to S, a process which generally proceeds with ca. 98% retention of stereochemistry and returns chiral benzylic tertiary thiols in high enantiomeric ratios.

Original languageEnglish
Pages (from-to)3395-3397
Number of pages3
JournalChemical Communications
Volume47
Issue number12
Early online date17 Feb 2011
DOIs
Publication statusPublished - 28 Mar 2011

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