Method for Producing Single Enantiomer Epoxides by the Adh Reduction of a-Leaving Group-Substituted Ketones and Cyclization
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United States of America Patent
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Issued Date -
Aug 28, 2008
app pub date -
Jun 7, 2006
filing date -
Jun 18, 2005
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Abandoned
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Abstract
The invention relates to a method for producing single enantiomer epoxides by reducing .alpha.-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 LG may stand for F, Cl, Br, I, OSO.sub.2Ar, OSO.sub.2CH.sub.3, OSO.sub.2R or OP(O)OR.sub.2, and R.sub.1, R.sub.2 and R.sub.3, independently of one another, stand for hydrogen, a branched or unbranched, optionally substituted C.sub.1-C.sub.20-alkyl radical, symbolize an optionally randomly substituted C.sub.3-C.sub.1-10-cycloalkyl or alkenyl radical or a randomly substituted carbo- or heterocyclic aryl radical, or correspond to a radical from the group CO.sub.2R, CONR.sub.2, COSR, CS.sub.2R, C(NH)NR2, CN, CHaI.sub.3, ArO, ArS, RO, RS, CHO, OH, NHR, NR.sub.2, Cl, F, Br, I or SiR.sub.3.
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