Enantioselective NHC-Catalysed Formal [4+2] Cycloaddition of Alkylarylketenes with beta, gamma-Unsaturated alpha-Ketophosphonates

Stuart Minto Leckie, Charlene Fallan, James Edward Taylor, T. Bruce Brown, David Pryde, Tomas Lebl, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

NHC-mediated enantioselective formal [4+2] cycloadditions of alkylarylketenes with gamma-substituted-beta,gamma-unsaturated alpha-ketophosphonates is described. A substrate-dependent switch in diastereoselectivity was observed, with gamma-aryl alpha-ketophosphonates providing preferentially the syn-dihydropyranone-phosphonates and gamma-methyl alpha-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
Pages (from-to)1243-1249
Number of pages7
JournalSynlett
Volume24
Issue number10
DOIs
Publication statusPublished - Jun 2013

Keywords

  • N-heterocyclic carbenes
  • cycloaddition
  • asymmetric catalysis
  • asymmetric synthesis
  • lactones
  • N-HETEROCYCLIC CARBENE
  • C-CARBOXYL TRANSFER
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • MICHAEL ADDITION
  • ASYMMETRIC ORGANOCATALYSIS
  • NUCLEOPHILIC CARBENES
  • DISUBSTITUTED KETENES
  • CHIRAL ALCOHOLS
  • ESTERS
  • ACYL

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