Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

Takanori Shibata, Hikaru Tarumi, Tsuneomi Kawasaki, Kenso Soai

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

Original languageEnglish
Pages (from-to)1023-1027
Number of pages5
JournalTetrahedron Asymmetry
Volume23
Issue number14
DOIs
Publication statusPublished - 2012 Jul 31

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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