Baker's yeast mediated reduction of substituted acenaphthenequinones: Regio- and enantioselective preparation of mono-hydroxyacenaphthenones

Abstract

Baker's yeast mediated reduction of acenaphthenequinone within 4–10 h afforded mono-hydroxyacenaphthenone mainly with low enantioselectivity, the substrate and mono-hydroxyacenaphthenone product almost converted to dihydroxyacenaphthene after 48 h. By control of the reaction time and in the presence of DMF as co-solvent, the reduction of 6-substituted acenaphthenequinones under vigorous agitation afforded the corresponding 2-hydroxyacenaphthenones in 24–84% yields with 10–93% ee.