Issue 12, 2011
From the journal:

Chemical Communications

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates†

Paul MacLellana  and  Jonathan Clayden*a  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK
E-mail: clayden@man.ac.uk

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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Article information

DOI
https://doi.org/10.1039/C0CC04912C
Article type
Communication
Submitted
11 Nov 2010
Accepted
02 Feb 2011
First published
17 Feb 2011

Chem. Commun., 2011,47, 3395-3397

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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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