Asymmetric Reduction with 5-Deazaflavin. III. : Reduction of Ethyl Benzoylformate in the Presence of Chiral Ligand

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概要

• 論文の詳細を見る

• A nonenzymatic asymmetric reduction of ethyl benzoylformate with an achiral 1,5-dihydro-5-deazaflavin derivative in chiral media was investigated as a model system for reruced nicotinamide adenine dinucleotide (phosphate)-dependent dihydrogenase. The chiral media include chiral nuclear magnetic resonance shift reagent, chiral Lewis acid, and a combination of metal ion an chiral ligand (additive). Of these reductions, a substantial asymmetric induction was observed in the presence of tris-[3-(heptafluoropropylhydroxymethylene)(+)-camphorato]europium to give ethyl mandelate possessing prediominantly S-configuration, in a optical yield of 24 to 36%. These values are among the highest so far reported in nonenzymatic reduction of ethyl benzoylformate with a 5-deazaflavin model. The discrimination of the prochiral face of the carbonyl compound was effectvie even when a catalytic amount of the chiral shift reagent was employed.

• 公益社団法人日本薬学会の論文
• 1990-03-25

著者

• 米田 文郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 田中 圭

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  静岡県大 薬

• 陳 星

  Faculty Of Pharmaceutical Sciences Kyoto University

• 木村 禎治

  Faculty of Pharmaceutical Sciences, Kyoto University

• 米田 文郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 川本 哲治

  Faculty of Pharmaceutical Sciences, Kyoto University

• 木村 禎治

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  京都大学薬学部

• 川本 哲治

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  Faculty of Eng., Oita Univ.

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