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|Type:||Artigo de periódico|
|Title:||Tuning Lipase-catalysed Kinetic Resolution Of 2-substituted Thiophenes And Furans: A Scalable Chemoenzymatic Route To Masked γ-bis-oxo-alcohols|
|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 chemo-enzymatic 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. © 2016 Elsevier B.V. All rights reserved.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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