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As model compounds for NADH coenzymes, three chiral Hantzsch ester-type dihydro-pyridines were prepared. By their use and 2,6-dimethyl-3,5-dicarbo-( — )-menthoxy-1,4-dihydropyridine that had already been prepared, asymmetric reductions of unactivated prochiral ketones were conducted under the action of alkali metal derivatives at room temperature in a non-polar solvent, and the alcohol product were obtained in a 36~80% chemical yield and 30~60% enantiomeric excess.
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