Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)The demand for greener and applicable approaches aiming at the synthesis of optically active compounds as single enantiomers has seen a significant growth worldwide. Since most of the chemically synthesized compounds are produced as racemates their kinetic resolution has been of great interest. For this purpose a number of chemo-enzymatic approaches were proposed. One of such approaches, the use of isolated lipases, is a well-established alternative. Herein we report the kinetic resolutions of 2 Substituted five-membered heteroaromatic rings. By optimizing the reaction conditions it was possible to produce (2-hydroxy)-2-substituted furans and thiophenes in high enantiomeric ratio (E> 200). Thus, racemic mixtures of compounds with slight structural differences were resolved. The current chemoenzymatic strategy has been applied to a scalable approach leading to the formation of the enantiopure (S)-2i a well-known building block used for the synthesis of bioactive natural compounds. (C) 2016 Elsevier B.V. All rights reserved.1263745CNPqFACEPECAPESINCT-INAMIConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)