Highly enantioselective asymmetric autocatalysis of pyrimidin-5-yl alkanol induced by chiral 1,3-disubstituted hydrocarbon allenes

Itaru Sato, Yohei Matsueda, Kousuke Kadowaki, Shigeru Yonekubo, Takanori Shibata, Kenso Soai

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

1,3-Disubstituted chiral allenes without any heteroatoms act as chiral initiators in the addition of (i-Pr)2Zn to pyrimidine-5-carbaldehyde to afford, in combination with the subsequent asymmetric autocatalysis, chiral pyrimidin-5-yl alkanols with up to 98% ee. The absolute configuration of the pyrimidin-5-yl alkanol formed depend on that of the chiral allene.

Original languageEnglish
Pages (from-to)3383-3387
Number of pages5
JournalHelvetica Chimica Acta
Volume85
Issue number10
DOIs
Publication statusPublished - 2002 Nov 26

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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