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Issue 12, 2011
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Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

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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.

Graphical abstract: Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

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Supplementary files

Article information


Submitted
11 Nov 2010
Accepted
02 Feb 2011
First published
17 Feb 2011

Chem. Commun., 2011,47, 3395-3397
Article type
Communication

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

P. MacLellan and J. Clayden, Chem. Commun., 2011, 47, 3395
DOI: 10.1039/C0CC04912C

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