American Chemical Society
jo101962v_si_001.pdf (1.03 MB)

Complementary Lipase-Mediated Desymmetrization Processes of 3-Aryl-1,5-Disubstituted Fragments. Enantiopure Synthetic Valuable Carboxylic Acid Derivatives

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journal contribution
posted on 2011-02-04, 00:00 authored by Nicolás Ríos-Lombardía, Vicente Gotor-Fernández, Vicente Gotor
Desymmetrizaton enzymatic processes have been extensively studied searching for optimal methods of producing enantioenriched monoacetates from prochiral diols and diesters. AK lipase has been found as an excellent biocatalyst for the desymmetriaztion of a series of previously synthesized 3-arylpentane-1,5-diols derivatives. The access to (S)- or (R)-monoacetates in high optical purity (86−99% ee) has been possible by using acetylation or hydrolysis reactions, respectively, where the reaction parameters have been optimized in terms of source and amount of biocatalyst, temperature, solvent, and reaction time. The synthetic potential of enantiopure monoesters has been demonstrated by using these interesting chiral building blocks for the preparation of novel enantiopure carboxylic acid derivatives.