Issue 51, 2014

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
08 4 2014
Accepted
06 5 2014
First published
06 5 2014

Chem. Commun., 2014,50, 6754-6757

Author version available

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

G. Mingat, J. J. W. McDouall and J. Clayden, Chem. Commun., 2014, 50, 6754 DOI: 10.1039/C4CC02596B

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