(132f) Asymmetric Reduction of Alpha–Hydroxy Aromatic Ketones to Chiral Aryl Vicinal Diols Using Carrot Enzymatic System

Xu, J. - Presenter, East China University of Science and Technology

Chiral aryl vicinal diols with special functional group are potentially valuable synthetic intermediates for the preparation of pharmaceuticals, agrochemicals and pheromones. The reduction of biocatalytic carbonyl to enantiomerically-pure secondary alcohols is one of the most convenient methods for establishing chirality. In this paper asymmetric reduction of α–hydroxy aromatic ketones was carried out by using carrot enzymatic system and chiral vicinal diols with special functional group were received. The optimal reaction conditions were gained after the investigation of various influencing factors. Chiral aryl vicinal diols were obtained with good yield and excellent enantiomeric excess under the appropriate conditions. Meanwhile, the steric factors and electronic effects of the substituents at the aromatic ring were shown to have an interesting effect on the yield and enantioselectivity.