Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

Gaëlle Mingat; Joseph J W McDouall; Jonathan Clayden

doi:10.1039/c4cc02596b

Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

Gaëlle Mingat, Joseph J W McDouall, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

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

18 Citations (Scopus)

Abstract

Stereospecific [3,3]-sigmatropic rearrangement of O-substituted thiocarbamate derivatives of enantiopure allylic alcohols provides allylic thiocarbamates as single enantiomers. Intramolecular arylation by rearrangement of their allyllithium derivatives provides allylic tertiary thiols. Allylation and ring-closing metathesis gives 2,5-dihydrothiophenes containing sulfur-bearing quaternary centres. This journal is

Original language	English
Pages (from-to)	6754-6757
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	51
Early online date	6 May 2014
DOIs	https://doi.org/10.1039/c4cc02596b
Publication status	Published - 28 Jun 2014

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Organic & Biological

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abstract = "Stereospecific [3,3]-sigmatropic rearrangement of O-substituted thiocarbamate derivatives of enantiopure allylic alcohols provides allylic thiocarbamates as single enantiomers. Intramolecular arylation by rearrangement of their allyllithium derivatives provides allylic tertiary thiols. Allylation and ring-closing metathesis gives 2,5-dihydrothiophenes containing sulfur-bearing quaternary centres. This journal is",

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T1 - Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

AU - Mingat, Gaëlle

AU - McDouall, Joseph J W

AU - Clayden, Jonathan

PY - 2014/6/28

Y1 - 2014/6/28

N2 - Stereospecific [3,3]-sigmatropic rearrangement of O-substituted thiocarbamate derivatives of enantiopure allylic alcohols provides allylic thiocarbamates as single enantiomers. Intramolecular arylation by rearrangement of their allyllithium derivatives provides allylic tertiary thiols. Allylation and ring-closing metathesis gives 2,5-dihydrothiophenes containing sulfur-bearing quaternary centres. This journal is

AB - Stereospecific [3,3]-sigmatropic rearrangement of O-substituted thiocarbamate derivatives of enantiopure allylic alcohols provides allylic thiocarbamates as single enantiomers. Intramolecular arylation by rearrangement of their allyllithium derivatives provides allylic tertiary thiols. Allylation and ring-closing metathesis gives 2,5-dihydrothiophenes containing sulfur-bearing quaternary centres. This journal is

UR - https://www.scopus.com/pages/publications/84901815976

U2 - 10.1039/c4cc02596b

DO - 10.1039/c4cc02596b

M3 - Article (Academic Journal)

C2 - 24831495

AN - SCOPUS:84901815976

SN - 1359-7345

VL - 50

SP - 6754

EP - 6757

JO - Chemical Communications

JF - Chemical Communications

IS - 51

ER -

Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

Abstract

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