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

84 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

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Borohydrides
Cobalt
Alcohols
Catalysts
Imines
Ketones
Methanol
Ethanol
Ligands
Kinetics

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Yamada, T., Nagata, T., Sugi, K. D., Yorozu, K., Ikeno, T., Ohtsuka, Y., ... Mukaiyama, T. (2003). Enantioselective borohydride reduction catalyzed by optically active cobalt complexes. Chemistry - A European Journal, 9(18), 4485-4509. https://doi.org/10.1002/chem.200304794

Enantioselective borohydride reduction catalyzed by optically active cobalt complexes. / Yamada, Tohru; Nagata, Takushi; Sugi, Kiyoaki D.; Yorozu, Kiyotaka; Ikeno, Taketo; Ohtsuka, Yuhki; Miyazaki, Daichi; Mukaiyama, Teruaki.

In: Chemistry - A European Journal, Vol. 9, No. 18, 22.09.2003, p. 4485-4509.

Research output: Contribution to journalArticle

Yamada, T, Nagata, T, Sugi, KD, Yorozu, K, Ikeno, T, Ohtsuka, Y, Miyazaki, D & Mukaiyama, T 2003, 'Enantioselective borohydride reduction catalyzed by optically active cobalt complexes', Chemistry - A European Journal, vol. 9, no. 18, pp. 4485-4509. https://doi.org/10.1002/chem.200304794
Yamada, Tohru ; Nagata, Takushi ; Sugi, Kiyoaki D. ; Yorozu, Kiyotaka ; Ikeno, Taketo ; Ohtsuka, Yuhki ; Miyazaki, Daichi ; Mukaiyama, Teruaki. / Enantioselective borohydride reduction catalyzed by optically active cobalt complexes. In: Chemistry - A European Journal. 2003 ; Vol. 9, No. 18. pp. 4485-4509.
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