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Type: Artigo
Title: Tuning Lipase-catalysed Kinetic Resolution Of 2-substituted Thiophenes And Furans: A Scalable Chemoenzymatic Route To Masked Gamma-bis-oxo-alcohols
Author: Ferreira
Dartagnam S. P.; Ferreira
Jeiely G.; Filho
Everaldo F. S.; Princival
Jefferson L.
Abstract: 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.
Subject: Biocatalysis
Organic Synthesis
Building Blocks
Editor: Elsevier Science BV
Rights: fechado
Identifier DOI: 10.1016/j.molcatb.2016.01.014
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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