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^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

35 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 language	English
Pages (from-to)	3395-3397
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	12
Early online date	17 Feb 2011
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.",

author = "Paul MacLellan and Jonathan Clayden",

year = "2011",

month = mar,

day = "28",

doi = "10.1039/c0cc04912c",

language = "English",

volume = "47",

pages = "3395--3397",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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TY - JOUR

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

AU - MacLellan, Paul

AU - Clayden, Jonathan

PY - 2011/3/28

Y1 - 2011/3/28

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=79952369434&partnerID=8YFLogxK

U2 - 10.1039/c0cc04912c

DO - 10.1039/c0cc04912c

M3 - Article (Academic Journal)

C2 - 21331400

AN - SCOPUS:79952369434

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

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