Enantioselective autemultiplication of chiral molecules by asymmetric autocatalysis

Kenso Soai, Takanori Shibata, Itaru Sato

Research output: Contribution to journalArticle

297 Citations (Scopus)

Abstract

Asymmetric autocatalysis is a process of automultiplication of a chiral compound in which chiral product acts as a chiral catalyst for its own production. The discovery and the development of asymmetric autocatalysis of pyrimidyl-, quinolyl-, and pyridylalkanois are described in the enantioselective additions of diisopropylzinc to the corresponding nitrogen- containing aldehydes. (Alkynylpyrimidyl)alkanols automultiply with a yield of over 99% and over 99.5% ee. Asymmetric autocatalysts with extremely low ee's automultiply with significant amplification of ee's without the need for any other chiral auxiliaries. Small enantiomeric imbalances of chiral molecules induced by physical factors can be amplified by the present asymmetric autocatalysis.

Original languageEnglish
Pages (from-to)382-390
Number of pages9
JournalAccounts of Chemical Research
Volume33
Issue number6
DOIs
Publication statusPublished - 2000 Jul 19
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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