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Issue 51, 2014
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Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

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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.

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

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Publication details

The article was received on 08 Apr 2014, accepted on 06 May 2014 and first published on 06 May 2014


Article type: Communication
DOI: 10.1039/C4CC02596B
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Citation: Chem. Commun., 2014,50, 6754-6757
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    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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