Stereoselective epoxidation of alkenes by chloroperoxidase

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...

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435192, 435280, C12N 908, C12P 1702

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053588606

ABSTRACT:
A method of converting olefins to chiral epoxides comprises combining an asymmetric aliphatic or aryl alkene substrate with a buffered chloroperoxidase solution to form a stabilized reaction mixture, and gradually adding hydrogen peroxide as a substrate oxidant, such that the chloroperoxidase catalyzes the conversion of the substrate to the corresponding epoxide in enantiomeric excess. The products of the invention are alkyl and aryl non-primary epoxides. The resulting preparations are enantiomerically pure, and may greatly enhance large-scale synthesis of stereoisomer products such as pharmaceuticals and pesticides.

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