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

Research output: Contribution to journalArticle (Academic Journal)

14 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 languageEnglish
Pages (from-to)6754-6757
Number of pages4
JournalChemical Communications
Volume50
Issue number51
Early online date6 May 2014
DOIs
Publication statusPublished - 28 Jun 2014

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