Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine

• Li Zhao

  Institute of Microbial Chemistry

• Kumagai Naoya

  Institute of Microbial Chemistry

• Shibasaki Masakatsu

  Institute of Microbial Chemistry

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.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 68 (6), 552-554, 2020-06-01

  The Pharmaceutical Society of Japan

Keywords

• 1,3-dipolar cycloaddition
• indium
• 7-azaindoline
• amide
• enantioselective

Details

• CRID: 1390848250114620672
• NII Article ID: 130007850053
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c20-00130
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 030429696
• PubMed: 32475860
• Web Site: http://id.ndl.go.jp/bib/030429696
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030429696
• Web Site: https://www.jstage.jst.go.jp/article/cpb/68/6/68_c20-00130/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed