Issue 0, 1980

NADH model reaction. Importance of hydroxy-groups in the asymmetric reduction of ethyl benzoylformate

Abstract

Ethyl benzoylformate has been reduced with an NADH analogue, N-{(1S)-2-hydroxy-1-[(S)-α-hydroxybenzyl]ethyl}-1-propyl-1,4-dihydronicotinamide, to give (S)-mandelate in 2.9–28.5% e.e. The asymmetric yield was remarkably affected by the amount of magnesium perchlorate present and continuously changed throughout the reaction. The possible functions of hydroxy-groups in the model compound are discussed in the light of the resultant stereochemical outcome.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 7-10

NADH model reaction. Importance of hydroxy-groups in the asymmetric reduction of ethyl benzoylformate

T. Makino, T. Nunozawa, N. Baba, J. Oda and Y. Inouye, J. Chem. Soc., Perkin Trans. 1, 1980, 7 DOI: 10.1039/P19800000007

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