A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

Chonticha Suttibut, Yoshihito Kohari, Ko Igarashi, Hiroto Nakano, Masafumi Hirama, Chigusa Seki, Haruo Matsuyama, Koji Uwai, Nobuhiro Takano, Yuko Okuyama, Kenichi Osone, Mitsuhiro Takeshita, Eunsang Kwon

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins.

Original languageEnglish
Pages (from-to)4745-4748
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number37
DOIs
Publication statusPublished - 2011 Sep 14

Keywords

  • 1,2-Dihydropyridine
  • Diels-Alder reaction
  • Isoquinuclidine
  • Organocatalyst
  • β-Amino alcohol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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