Simple Biocatalytic Access to Enantiopure (S)‐1‐Heteroarylethanols Employing a Microbial Hydrogen Transfer Reaction

Abstract

Abstract Lyophilised cells of various Rhodococcus spp. were employed in an efficient hydrogen transfer‐like process for the asymmetric bioreduction of heteroaryl methyl ketones using 2‐propanol as hydrogen donor. Besides the genus Rhodococcus , only Mycoplana rubra R14 showed a comparable stability towards elevated concentrations of the co‐substrate 2‐propanol. Among the organisms tested, Rhodococcus ruber DSM 44541 and DSM 43338 showed best activity and selectivity. With these strains, the reaction proceeded with high stereoselectivity (ee>99%) and predictable stereochemical outcome regardless of the nature of the heteroaromatic ring system. The reaction could be performed at the exceptional substrate concentration of up to 0.4 mol L −1 in an environmentally friendly aqueous‐organic solvent mixture at room temperature and is easy to handle, thus providing a very practical tool to access enantiopure 1‐heteroarylethanols.

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Identifiers

DOI

10.1002/adsc.200303210

Journal

Advanced Synthesis & Catalysis

Year

2004