Direct Catalytic Asymmetric Mannich-Type Reaction of α-N3 Amide

Zhongdong Sun, Karin Weidner, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

An α-N3 7-azaindoline amide serves as a latent enolate to directly engage in an asymmetric Mannich-type reaction with N-thiophosphinoyl imines by the action of a cooperative catalyst. The thus-obtained highly enantioenriched anti-adduct was transformed into β-amino-α-azido acid in high yield by simple acidic treatment. Take it easy: An α-N3 7-azaindoline amide serves as a latent enolate to directly engage in an asymmetric Mannich-type reaction with N-thiophosphinoyl imines by the action of a cooperative catalyst. The thus-obtained highly enantioenriched anti-adduct was transformed into β-amino-α-azido acid in high yield by simple acidic treatment.

Original languageEnglish
Pages (from-to)17574-17577
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number49
DOIs
Publication statusPublished - 2015 Dec 1
Externally publishedYes

Keywords

  • amide
  • asymmetric catalysis
  • azide
  • enantioselective
  • Mannich

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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