Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Paul MacLellan; Jonathan Clayden

doi:10.1039/c0cc04912c

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Paul MacLellan
, Jonathan Clayden

Research output: Contribution to journal › Article › peer-review

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. © 2011 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	3395-3397
Number of pages	2
Journal	Chemical Communications
Volume	47
Issue number	12
DOIs	https://doi.org/10.1039/c0cc04912c
Publication status	Published - 28 Mar 2011

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title = "Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates",

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. {\textcopyright} 2011 The Royal Society of Chemistry.",

author = "Paul MacLellan and Jonathan Clayden",

year = "2011",

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doi = "10.1039/c0cc04912c",

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journal = "Chemical Communications",

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AU - MacLellan, Paul

AU - Clayden, Jonathan

PY - 2011/3/28

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N2 - 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. © 2011 The Royal Society of Chemistry.

AB - 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. © 2011 The Royal Society of Chemistry.

U2 - 10.1039/c0cc04912c

DO - 10.1039/c0cc04912c

M3 - Article

SN - 1359-7345

VL - 47

SP - 3395

EP - 3397

JO - Chemical Communications

JF - Chemical Communications

IS - 12

ER -

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Abstract

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