High substrate/catalyst organocatalysis by a chiral Brønsted acid for an enantioselective aza-ene-type reaction

Masahiro Terada, Kyoko Machioka, Keiichi Sorimachi

Research output: Contribution to journalArticlepeer-review

236 Citations (Scopus)

Abstract

(Chemical Equation Presented) Lowering the load: A very small amount of a binaphthol-derived monophosphoric acid organocatalyst accelerates an azaene-type reaction of N-benzoylimines with enecarbamates to provide β-aminoimines with high enantiomeric purity. This catalysis with a high substrate/catalyst(S/ C) ratio provides a practical route to 1,3-diamine derivatives of synthetic and biological importance.

Original languageEnglish
Pages (from-to)2254-2257
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number14
DOIs
Publication statusPublished - 2006 Mar 27

Keywords

  • Asymmetric synthesis
  • Brønsted acids
  • Ene reaction
  • Organocatalysis
  • Phosphoric acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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