Synthesis of an enantiocomplementary catalyst of β-isocupreidine (β-ICD) from quinine

Ayako Nakano, Mina Ushiyama, Yoshiharu Iwabuchi, Susumi Hatakeyama

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

Compound 20, a pseudoenantiomer of β-isocupreidine (β-ICD), was synthesized from quinine employing a Barton reaction of nitrosyl ester 13 and acid-catalyzed cyclization of carbinol 18 as key steps. The Baylis-Hillman reaction of benzaldehyde, p-nitrobenzaldehyde, and hydrocinnamaldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) using 20 as a chiral amine catalyst was found to give the corresponding S-enriched adducts in high optical purity (> 91% ee) in contrast to the β-ICD-catalyzed reaction which affords R-enriched adducts. This result suggests that compound 20 can serve as an enantiocomplementary catalyst of β-ICD in the asymmetric Baylis-Hillman reaction of aldehydes with HFIPA.

Original languageEnglish
Pages (from-to)1790-1796
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume347
Issue number14
DOIs
Publication statusPublished - 2005 Nov 1
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Baylis-Hillman reaction
  • Organic catalysis
  • Quinine
  • β-isocupreidine

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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