A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine

Hiroto Nakano, Kenichi Osone, Mitsuhiro Takeshita, Eunsang Kwon, Chigusa Seki, Haruo Matsuyama, Nobuhiro Takano, Yoshihito Kohari

Research output: Contribution to journalArticlepeer-review

88 Citations (Scopus)

Abstract

Enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a novel chiral oxazolidine organocatalyst afforded chiral isoquinuclidines that is an efficient synthetic intermediate of oseltamivir, with fairly good chemical yield and excellent enantioselectivity (90%, up to >99% ee).

Original languageEnglish
Pages (from-to)4827-4829
Number of pages3
JournalChemical Communications
Volume46
Issue number26
DOIs
Publication statusPublished - 2010 Jul 14

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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