Biocatalysed Stereoselective Synthesis of Chiral Nitro Alcohols

Abstract

Chiral nitro alcohols are versatile intermediates used in the synthesis of important pharmaceuticals and chiral synthones. During the past decade, the search for greener and more sustainable synthetic procedures has promoted the investigation of biocatalysed strategies for the synthesis of enantiopure nitro alcohols. In this article, stereoselective synthesis of chiral nitro alcohols by biocatalytic reduction of acetophenone and 2-, 3-, 4-nitro acetophenone, 3-nitro-4-methyl acetophenone and 3-nitro propiophenone was accomplished using Rhizopus arrhizus NCIM 878 to yield corresponding (S) -nitro alcohols in good yield and ee (70-87%). However, the biotransformation is very sensitive to the effect of substituent methyl group on aromatic ring and on side chain which proves its structure-activity relationship.