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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10.1039/c0cc04912c

CCDC 781954: Experimental Crystal Structure Determination
MacLellan, P. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2011
DOI: 10.5517/ccv7pb2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccv7pb2&sid=DataCite
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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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day = "28",

doi = "10.1039/c0cc04912c",

language = "English",

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publisher = "Royal Society of Chemistry",

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T1 - Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

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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CCDC 781954: Experimental Crystal Structure Determination

Cite this