Tuning Lipase-catalysed Kinetic Resolution of 2-Substituted thiophenes and furans. A Scalable Chemoenzymatic route to masked γ-Bis-Oxo-alcohols.

Publication date: Available online 3 February 2016 Source:Journal of Molecular Catalysis B: Enzymatic Author(s): Dartagnan S.P. Ferreira, Jeiely G. Ferreira, Everaldo F.S. Filho, Jefferson L. Princival 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. Graphical abstract

Source: Journal of Molecular Catalysis B: Enzymatic - February 4, 2016 Category: Biochemistry Source Type: research