Asymmetric amplification using chiral cocrystals formed from achiral organic molecules by asymmetric autocatalysis

Tsuneomi Kawasaki, Kazumichi Jo, Hirotaka Igarashi, Itaru Sato, Masaki Nagano, Hideko Koshima, Kenso Soai

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

(Chemical Equation Presented) Enantioselective addition of diisopropyl-zinc to a pyrimidine-5-carbaldehyde was induced by chiral cocrystals of achiral two-component molecular crystals of tryptamine/para-chlorobenzoic acid (see scheme) and 3-indolepropionic acid/ phenanthridine. This reaction, in conjunction with asymmetric autocatalysis, afforded a pyrimidyl alkanol in high enantiomeric excess.

Original languageEnglish
Pages (from-to)2774-2777
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number18
DOIs
Publication statusPublished - 2005 Apr 29
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Autocatalysis
  • Chirality
  • Cocrystals
  • Zinc

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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