Intramolecular vinylation of carbanions using N-acyl benzomorpholines as masked vinylureas and vinylcarbamates

Brian Corbet, Johnathan Matlock, Josep Mas Rosello, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

2 Citations (Scopus)
228 Downloads (Pure)

Abstract

Treatment of urea or carbamate derived benzomorpholines with LDA generates N-vinylureas or N-vinylcarbamates by elimination of a phenoxide anion, cleaving the benzomorpholine ring. Simultaneous formation of a carbanion  to an aryl or nitrile stabilising group allows migration of the newly-formed N-vinyl substituent to the carbanionic centre, in some cases with high enantiospecificity. Mild hydrolysis of the resulting urea or carbamate returns a C-vinylated amine, alcohol or hydantoin, in some cases with high enantiomeric purity. This ‘masked’ vinylation strategy avoids the need to use the reactive and volatile vinyl isocyanate as a starting material.
Original languageEnglish
Pages (from-to)634-642
Number of pages9
JournalComptes Rendus Chimie
Volume20
Issue number6
Early online date13 Mar 2017
DOIs
Publication statusPublished - 1 Jun 2017

Keywords

  • Vinylation
  • Benzomorpholine
  • Benzylic anions
  • Tertiary stereocentre
  • Hydantoin

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