Enantioselective NHC-catalysed formal [4+2] cycloaddition of alkylaryl-ketenes with β,γ-unsaturated α-ketophosphonates

Stuart M. Leckie, Charlene Fallan, James E. Taylor, T. Bruce Brown, David Pryde, Tomáš Lébl, Alexandra M.Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

NHC-mediated enantioselective formal [4+2] cycloadditions of alkylarylketenes with γ-substituted-β,γ-unsaturated α-ketophosphonates is described. A substrate-dependent switch in diastereoselectivity was observed, with γ-aryl α-ketophosphonates providing preferentially the syn-dihydropyranone-phosphonates and γ-methyl α-ketophosphonates favouring the anti-dihydropyranone-phosphonate. In addition, ketene generation in situ retained high levels of stereoselectivity and led to improved product yields when compared with the corresponding two-step procedure.

Original languageEnglish
Article numberST-2013-R0288-C
Pages (from-to)1243-1249
Number of pages7
JournalSynlett
Volume24
Issue number10
Early online date28 May 2013
DOIs
Publication statusPublished - 31 May 2013

Keywords

  • asymmetric catalysis
  • asymmetric synthesis
  • cycloaddition
  • lactones
  • N-heterocyclic carbenes

ASJC Scopus subject areas

  • Organic Chemistry

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