Patent ID: 6365398
Filing Date: 2002-04-02
Classification: C12P

Abstract:
A process for the preparation of stereoisomeric carboxylic acid esters of the general formula I where the substituents and variables have the meanings* is a possible chiral center, n, m, p independently of one another are 0 or 1, X is an unsubstituted or Fâ€”, Clâ€”, Brâ€”, Iâ€”, NO2â€” or C1-C4-alkoxy-substituted C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl or C3-C8-cycloalkenyl, C6-C14-aryl, C7-C16-alkylaryl, C8-C16-alkenylaryl, C8-C16-alkynylaryl, C7-C18-arylalkyl, C8-C18-arylalkenyl, C8-C18-arylalkynyl or C4-C12-heteroaryl radical or a substituted C6-C14-aryl, C7-C16-alkylaryl, C8-C16-alkenylaryl, C8-C16-alkynylaryl, C7-C18-arylalkyl, C8-C18-arylalkenyl, C8-C18-arylalkynyl or C4-C12-heteroaryl radical, where in each case two adjacent aryl substituents can together form a further substituted or unsubstituted aromatic, saturated or partially saturated ring having 5 to 6 atoms in the ring, which can contain one or more heteroatoms such as O, N or S, Y is â€”CH2â€”, â€”COâ€”, oxygen or sulfur, R2 is a substituted or unsubstituted, branched or unbranched C1-C6-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C6-C14-aryl or C4-C12-heteroaryl radical, R3, R4, R5 independently of one another are hydrogen, a hydroxyl, halogen, cyano, nitro or amino radical or a substituted or unsubstituted, branched or unbranched C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C3-C10-cycloalkyl, C3-C10-cycloalkyloxy, C6-C14-aryl, C7-C18-alkylaryl, C4-C12-heteroaryl or C5-C16-alkylheteroaryl radical or a substituted or unsubstituted olefinic or aromatic acyl radical or two adjacent substituents R3, R4 and R5 can together form a further substituted or unsubstituted aromatic, saturated or partially saturated ring having 5 to 6 atoms, which can contain one or more heteroatoms such as O, N or S, R6 is hydrogen or a substituted or unsubstituted, branched or unbranched C1-C6-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C6-C14-aryl or C4-C12-heteroaryl radical and R7 is hydrogen or a substituted or unsubstituted, branched or unbranched C1-C6-alkyl, C1-C4-alkoxy or C3-C6-cycloalkyl radical, where in the case where p=0, R7 is not hydrogen or X and in the case where p=1, either R6 or R7 is hydrogen, but not both are simultaneously hydrogen and in the case where R7=hydrogen, R6 is not X and in the case where R7 is not hydrogen, R6 is hydrogen or X, which comprises reacting a racemic carboxylic acid ester of the general formula II whereR1 is hydrogen or C1-C4-alkyl, with a racemic alcohol of the general formula IIII in the presence of a carboxyl ester hydrolase (EC 3.1.1).