Highly stereoselective [4+2] cycloaddition of azlactones to β,γ-unsaturated α-ketoesters catalyzed by an axially chiral guanidine base

Masahiro Terada, Hiroyuki Nii

Research output: Contribution to journalArticlepeer-review

57 Citations (Scopus)

Abstract

Sweet catalysis! The enantio-and diastereoselective cycloaddition reaction of azlactones with β,γ-unsaturated α-ketoesters was demonstrated by taking advantage of the multiple reactive sites on the azlactone with the use of an axially chiral guanidine-base catalyst. The most likely reaction pathway involves three consecutive steps to provide a facile access to α-amino δ-lactones with a sugar framework in a highly stereoselective manner (see scheme).

Original languageEnglish
Pages (from-to)1760-1763
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number6
DOIs
Publication statusPublished - 2011 Dec 7

Keywords

  • amino sugar
  • asymmetric catalysis
  • cycloaddition
  • guanidine
  • organocatalysis

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