Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate

Masahiro Terada, Kazuyo Soga, Norie Momiyama

Research output: Contribution to journalArticle

126 Citations (Scopus)

Abstract

(Chemical Equation Presented) Double interaction doesit: Highly enantio- and diastereoselective aza-ene-type reaction of glyoxylate with an enecarbamate is accomplished by using a binol-derived phosphoric acid catalyst (see scheme). DFT computational analysis revealed that two hydrogen bonds formed between the catalyst and the aldehyde are critical for the high enantioselectivity.

Original languageEnglish
Pages (from-to)4122-4125
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number22
DOIs
Publication statusPublished - 2008 May 19

Keywords

  • Asymmetric catalysis
  • Brønsted acids
  • Ene reactions
  • Phosphoric acids
  • Transition states

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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