Direct Catalytic Asymmetric Aldol Reaction of an α-Azido Amide

Karin Weidner, Zhongdong Sun, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

A direct aldol reaction of an α-azido 7-azaindolinylamide, promoted by a Cu-based cooperative catalyst, is documented. Aromatic aldehydes bearing an ortho substituent exhibited diastereodivergency depending on the nature of the chiral ligands used. Smooth reactions with ynals highlighted the broad substrate scope. A vicinal azido alcohol unit in the product allowed direct access to the corresponding aziridine and facile hydrolysis of the 7-azaindolinylamide moiety furnished enantioenriched β-hydroxy-α-azido carboxylic acid derivatives.

Original languageEnglish
Pages (from-to)6236-6240
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number21
DOIs
Publication statusPublished - 2015 May 18
Externally publishedYes

Keywords

  • aldol reaction
  • amides
  • asymmetric catalysis
  • azides
  • copper

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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