Highly enantioselective asymmetric autocatalysis induced by chiral ionic crystals of sodium chlorate and sodium bromate

Itaru Sato, Kousuke Kadowaki, Yasushi Ohgo, Kenso Soai

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)

Abstract

Chiral crystals of sodium chlorate and sodium bromate induced highly enantioselective organic synthesis in combination with asymmetric autocatalysis. (S)-5-Pyrimidyl alkanols with up to 98% ee were obtained in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehydes in the presence of d-sodium chlorate. On the other hand, (R)-5-pyrimidyl alkanols with up to 98% ee were obtained for the corresponding reaction in the presence of l-sodium chlorate. Chiral crystals of d- and l-sodium bromate were also found to work as chiral initiators.

Original languageEnglish
Pages (from-to)209-214
Number of pages6
JournalJournal of Molecular Catalysis A: Chemical
Volume216
Issue number2
DOIs
Publication statusPublished - 2004 Jul 12

Keywords

  • Asymmetric autocatalysis
  • Asymmetric synthesis
  • Crystals
  • Enantiomorphism
  • Surface

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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