Development of asymmetric cycloaddition reaction using amino alcohol and its derivative as an organocatalyst

Hiroto Nakano, Jun Kumagai, U. V.Subba Reddy, Chigusa Seki, Yuko Okuyama, Eunsang Kwon

Research output: Contribution to journalReview article

4 Citations (Scopus)

Abstract

The design of a chiral organocatalyst is very important for achievement of a high optical purity in a catalytic asymmetric reaction. Recently, we developed various chiral β-amino alcohol organocatalysts. These organocatalysts showed high levels of catalytic activity in the asymmetric Diels-Alder (DA) reactions of some dienes with dienophiles and 1,3-dipolar cycloaddition of some nitrones with α,β-unsaturated aldehydes, respectively. Especially, β-amino alcohols worked as organocatalyst in the DA reaction of 1,2-dihydropyridines with acroleins to afford the useful synthetic intermediate of Tamiflu. The review summarizes these our studies.

Original languageEnglish
Pages (from-to)720-731
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume74
Issue number7
DOIs
Publication statusPublished - 2016 Jan 1
Externally publishedYes

Keywords

  • 1,2-Dihydropyridine
  • 1,3-dipolar cycloaddition
  • Anthrone
  • Diels-Alder reaction
  • Isoquinuclidines
  • Isoxazolidine
  • Nitrones
  • Organocatalyst
  • Oxazolidine
  • Tamiflu
  • β-Amino alcohol

ASJC Scopus subject areas

  • Organic Chemistry

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