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Chemoenzymatic functionalization of cyclic 1,2-diketones

Biçer, Işıl
Chiral hydroxylated cyclopentane derivatives are important structural units in many biologically active compounds and are also important synthons for the asymmetric synthesis of natural products. Synthesis of these types of compounds in optically pure form found increased interest in pharmaceutical chemistry. For this purpose 5-acetoxy-3-methyl-2-methoxy-2-cyclopentene-1-one and 5-acetoxy-3-ethyl-2-methoxy-2-cyclopentene-1-one were acetoxylated using manganese (III) acetate at a’ positions. Enzyme catalyzed enantioselective hydrolysis of hydrolyzed acetoxy derivatives gives the corresponding hydroxylated diketones in optically pure form.