Chemical and Pharmaceutical Bulletin p. 616 - 618 (1990)
Update date:2022-09-26
Topics:
Tanaka
Kimura
Chen
Kawamoto
Yoneda
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 reduced 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 and 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 predominantly S-configuration, in an 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 effective even when a catalytic amount of the chiral shift reagent was employed.
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