METHOD FOR PRODUCING SINGLE ENANTIOMER EPOXIDES BY THE ADH REDUCTION OF ALPHA-LEAVING GROUP-SUBSTITUTED KETONES AND CYCLISATION

摘要

The invention relates to a method for producing single enantiomer epoxides by reducing a-leaving group-substituted ketones with (R)- or (S)-selective alcohol dehydrogenases in the presence of a cofactor and optionally a suitable system for regenerating the oxidised cofactor, to produce the corresponding single enantiomer alcohols and subsequently, by means of cyclisation induced by a base, the corresponding single enantiomer epoxides (EQUATION 1 ), wherein in EQUATION 1 LG may stand for F, CI, Br, I, OSO2Ar, OSO2CH3, OSO2R or OP(O)OR2, and R1, R2 and R3, independently of one another, stand for hydrogen, a branched or unbranched, optionally substituted C1-C2O- alkyl radical, symbolise an optionally randomly substituted C3-C10- cycloalkyl or alkenyl radical or a randomly substituted carbo- or heterocyclic aryl radical, or corresponds to a radical from the group CO2R, CONR2, COSR, CS2R, C(NH)NR2, CN, CHaI3, ArO, ArS, RO, RS, CHO, OH, NHR, NR2, Cl, F, Br, I or SiR3.