Enantioselective borohydride reduction catalyzed by optically active cobalt complexes

Tohru Yamada, Takushi Nagata, Kiyoaki D. Sugi, Kiyotaka Yorozu, Taketo Ikeno, Yuhki Ohtsuka, Daichi Miyazaki, Teruaki Mukaiyama

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

The highly enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing the appropriate alcohol as modifiers and a suitable β-ketoiminato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the preparation of optically active 1,3-diols, the stereoselective reduction of diacylferrocenes, and dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds.

Original languageEnglish
Pages (from-to)4485-4509
Number of pages25
JournalChemistry - A European Journal
Volume9
Issue number18
DOIs
Publication statusPublished - 2003 Sep 22

Keywords

  • Asymmetric catalysis
  • Diastereoselectivity
  • Enantioselectivity
  • Kinetic resolution
  • Reduction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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