Asymmetric automultiplication of chiral compounds by asymmetric autocatalysis

Kenso Soai, Itaru Sato, Takanori Shibata

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Asymmetric automultiplication of chiral compounds by asymmetric autocatalysis is realized for the first time where a chiral product acts as a chiral catalyst for its own production. Practically perfect asymmetric autocatalysis (>99%, >99.5% ee) is attained using pyrimidyl alkanol as an asymmetric autocatalyst in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde. Moreover, asymmetric autocatalyst with very low ee enhances its ee significantly up to > 99.5% ee during the automultiplicafion without the assistance of any other chiral auxiliaries. Amino acids and [6]helicene with very low ee which are produced by asymmtric photolysis and photosynthesis using circularly polarized light (CPL) serve as chiral initiators of asymmetric autocatalysis, and pyrimidyl alkanol with high ee is obtained. Inorganic chiral crystals such as quartz and sodium chlorate also work as chiral initiators. These results correlate for the first time the proposed origins of chirality of organic compounds such as CPL and quartz with the chirality of organic compounds with very high ee.

Original languageEnglish
Pages (from-to)668-678
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume60
Issue number7
DOIs
Publication statusPublished - 2002 Jul
Externally publishedYes

Keywords

  • Asymmetric autocatalysis
  • Automultiplication
  • Chirality
  • Circularly polarized light
  • Dialkylzinc
  • Enantioselective synthesis
  • Helicene
  • Isotope
  • Quartz
  • Sodium chlorate

ASJC Scopus subject areas

  • Organic Chemistry

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