Carbolithiation of S-alkenyl-N-aryl thiocarbamates: Carbanion arylation in a connective route to tertiary thiols

Daniele Castagnolo, Daniel J. Foley, Hatice Berber, Renzo Luisi, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

14 Citations (Scopus)

Abstract

S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.

Original languageEnglish
Pages (from-to)2116-2119
Number of pages4
JournalOrganic Letters
Volume15
Issue number9
Early online date15 Apr 2013
DOIs
Publication statusPublished - 3 May 2013

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