Enantioselective borohydride reduction catalyzed by optically active β-ketoiminato cobalt complexes

Tohru Yamada, Takushi Nagata, Yuhki Ohtsuka, Taketo Ikeno, Teruaki Mukaiyama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Optically active β-ketoiminato cobalt complexes were recently developed as high performance catalysts for enantioselective borohydride reduction of aromatic ketones or imines to afford the optically active alcohols or amines with high enantiomeric excesses. This enantioselective reduction is carried out using a precisely pre-modified borohydride with alcohols such as tetrahydrofur-furyl alcohol, ethanol and methanol, and high optical yields are realized by choosing the appropriate alcohol as modifiers and a suitable β-ketiominato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the efficient preparations of optically active 1,3-diaryl-1,3-propanediols, the stereoselective reduction of diacylferrocenes, and the dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds to afford the corresponding optically active anti-aldol compounds. In the presence of a catalytic amount of the cobalt complex and modified borohydride, the asymmetric 1,4-reduction of β,β-disubstituted α,β-unsaturated carboxamides proceeded with high enantioselectivity, and the 1,4-reduction of the α-substituted α,β-unsaturated carboxamides followed by enantioselective in situ protonation smoothly proceeded to afford the optically active α-substituted carboxamides with good enantiomeric excesses.

Original languageEnglish
Pages (from-to)843-856
Number of pages14
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume61
Issue number9
Publication statusPublished - 2003 Sep

Fingerprint

Borohydrides
Cobalt
Alcohols
Catalysts
Imines
Enantioselectivity
Protonation
Ketones
Amines
Methanol
Ethanol
Ligands
Kinetics

Keywords

  • Catalytic enantioselective protonation
  • Enantioselective 1,4-reduction
  • Enantioselective reduction
  • Optically active anti-aldol compound
  • Optically active cobalt complex catalyst
  • Optically active diol compound
  • Sodium borohydride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective borohydride reduction catalyzed by optically active β-ketoiminato cobalt complexes. / Yamada, Tohru; Nagata, Takushi; Ohtsuka, Yuhki; Ikeno, Taketo; Mukaiyama, Teruaki.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 61, No. 9, 09.2003, p. 843-856.

Research output: Contribution to journalArticle

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