Phosphorodiamidic acid as a novel structural motif of Brønsted acid catalysts for direct Mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds

Masahiro Terada, Keiichi Sorimachi, Daisuke Uraguchi

Research output: Contribution to journalArticle

79 Citations (Scopus)

Abstract

Phosphorodiamidic acid 1 was developed as an efficient Brønsted acid catalyst for the direct Mannich reaction of N-acyl imines with 1,3-dicarbonyl compounds. Phosphorodiamidic acids were proposed as a novel structural motif of enantioselective Br0nsted acid catalysts because they possess unique features, including the capability of introducing various substituents to the nitrogen atoms and the preparation from readily available chiral diamines in a short step. We demonstrated that chiral phosphorodiamidic acid 1b derived from binaphthalene bis(sulfonamide) functioned as an enantioselective catalyst to give the Mannich product in an optically active form.

Original languageEnglish
Article numberY07505ST
Pages (from-to)133-136
Number of pages4
JournalSynlett
Issue number1
DOIs
Publication statusPublished - 2006 Jan 5

Keywords

  • Asymmetric catalysis
  • Green chemistry
  • Imines
  • Mannich reaction
  • Organocatalyst

ASJC Scopus subject areas

  • Organic Chemistry

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