22426-24-0Relevant articles and documents
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Duveen,Kenyon
, p. 621 (1936)
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Tuning lipase-catalysed kinetic resolution of 2-substituted thiophenes and furans: A scalable chemoenzymatic route to masked γ-bis-oxo-alcohols
Ferreira, Dartagnan S.P.,Ferreira, Jeiely G.,Filho, Everaldo F.S.,Princival, Jefferson L.
, p. 37 - 45 (2016/02/18)
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.
Entrapment of Pseudomonas cepacia lipase with peracetylated β-cyclodextrin in sol-gel: Application to the kinetic resolution of secondary alcohols
Ghanem, Ashraf,Schurig, Volker
, p. 2547 - 2555 (2007/10/03)
Co-lyophilized Pseudomonas cepacia lipase with peracetylated β-cyclodextrin was immobilized by the sol-gel process. The gel-entrapped lipase/cyclodextrin was prepared by the hydrolysis of methyltrimethoxysilane (MTMS) in the presence of the co-lyophilized lipase with peracetylated β-cyclodextrin prepared with different weight ratios (enzyme to CD). This type of enzyme preparation was subsequently used in the kinetic resolution of a set of secondary alcohols using isopropenyl acetate as an innocuous acyl donor in toluene as the organic medium. The resulting chiral alcohols (substrate) and the corresponding acetates (product) were baseline separated in one analysis without derivatization using gas chromatography on a new chiral stationary phase (CSP) Chirasil-β-Dex containing an undecamethylene spacer (C11-Chirasil-Dex).