Catalytic asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated amide and Azomethine Imine

Zhao Li, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

α,β-Unsaturated amides were incorporated as viable dipolarophiles in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines. The use of a 7-Azaindoline auxiliary was essential to acquire sufficient reactivity with excellent diastereoselectivity, likely due to the chelating activation of the amide by the In(III)/ bishydroxamic acid complex. Although the enantioselectivity remains unsatisfactory, this work is an important step toward the development of an asymmetric catalysis utilizing stable and low-reactive substrates. Key words 1,3-dipolar cycloaddition; indium; 7-Azaindoline; amide; enantioselective.

Original languageEnglish
Pages (from-to)552-554
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume68
Issue number6
DOIs
Publication statusPublished - 2020
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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