title: Complementary lipase-mediated desymmetrization processes of 3-aryl-1,5-disubstituted fragments. Enantiopure synthetic valuable carboxylic acid derivatives.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, Spain.
authors.forename: Nicolás
authors.initials: N
authors.lastname: Ríos-Lombardía
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor-Fernández
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D009904:Optical Rotation; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D002264:Carboxylic Acids; D012997:Solvents; D008049:Lipase