One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

Hiroaki Gotoh, Hiroshi Ogino, Hayato Ishikawa, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Chiral bicyclo[3.3.0]octatrienes with excellent enantioselectivity were synthesized from the simple starting materials of α,β-unsaturated aldehyde and cyclopentadiene via one-pot operation, which consisted of a diphenylprolinol silyl ether-mediated ene-type reaction, intramolecular addition reaction of cyclopentadiene moiety with aldehyde and dehydration reaction.

Original languageEnglish
Pages (from-to)4894-4899
Number of pages6
JournalTetrahedron
Volume66
Issue number26
DOIs
Publication statusPublished - 2010 Jun 26

Keywords

  • Asymmetric reaction
  • One-pot reaction
  • Organocatalyst
  • ene-Reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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