NHC-mediated enantioselective formal [4 + 2] cycloadditions of alkylarylketenes and β,γ-unsaturated α-ketocarboxylic esters and amides

Stuart M. Leckie, T. Bruce Brown, David Pryde, Tomas Lebl, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Chiral N-heterocyclic carbenes (NHCs) promote the asymmetric formal [4 + 2] cycloaddition of alkylarylketenes with β,γ-unsaturated α-ketocarboxylic esters and amides. Divergent diastereoselectivity is observed in this process, with γ-aryl-β,γ-unsaturated α-ketocarboxylic esters and amides giving preferentially syn-dihydropyranones (up to 68:32 dr syn:anti, up to 98% ee), while γ-alkyl-derivatives generate anti-dihydropyranones (up to 18:82 dr syn:anti, up to 75% ee). © The Royal Society of Chemistry 2013.
Original languageEnglish
Pages (from-to)3230-3246
Number of pages17
JournalOrganic & Biomolecular Chemistry
Volume11
Issue number19
Early online date15 Apr 2013
DOIs
Publication statusPublished - 21 May 2013

Keywords

  • DIELS-ALDER REACTIONS
  • N-HETEROCYCLIC CARBENES
  • C-CARBOXYL TRANSFER
  • SILYL KETENE ACETALS
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • CATALYZED CYCLOADDITION
  • DISUBSTITUTED KETENES
  • OXAZOLYL CARBONATES
  • CHIRAL ALCOHOLS
  • O-CARBOXYL

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