Preparation of chiral trans-5-substituted-acenaphthene-1,2-diols by baker’s yeast-mediated reduction of 5-substituted-acenaphthylene-1,2-diones

A series of trans-5-substituted-acenaphthene-1,2-diols were obtained in 21–72% yield with 97–100% ee by baker’s yeast-mediated reduction of the corresponding acenaphthylene-1,2-diones, in the presence of DMSO as a co-solvent and under vigorous agitation. The absolute configuration of (−)-trans-5-methoxy-acenaphthene-1,2-diol trans-3b and (−)-trans-5-bromo-acenaphthene-1,2-diol trans-3c was assigned as (S,S) and (−)-trans-5-thiomorpholin-acenaphthene-1,2-diol trans-3d was established as (R,R) by exciton-coupled circular dichroism.

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trans-(1S,2S)-Acenaphthene-1,2-diolC12H10O2Ee = 97%[α]D20=-24.1 (c 0.28, CHCl3)Source of chirality: asymmetric redutionAbsolute configuration: (1S,2S)

trans-(1S,2S)-5-Methoxyacenaphthene-1,2-diolC13H12O3Ee = 100%[α]D20=-24.2 (c 0.26, CHCl3)Source of chirality: asymmetric redutionAbsolute configuration: (1S,2S)

trans-(1S,2S)-5-Bromoacenaphthene-1,2-diolC12H9BrO2Ee = 99%[α]D20=+15.1 (c 0.35, EtOAc)Source of chirality: asymmetric redutionAbsolute configuration: (1S,2S)

trans-(1R,2R)-5-Thiomorpholinacenaphthene-1,2-diolC16H17NO2SEe = 100%[α]D20=-29.6 (c 0.24, CHCl3)Source of chirality: asymmetric redutionAbsolute configuration: (1R,2R)