1248378-46-2Relevant academic research and scientific papers
Lipase-catalyzed asymmetric acylation in the chemoenzymatic synthesis of furan-based alcohols
Hara, Piia,Turcu, Mihaela-Claudia,Sundell, Riku,To?a, Monica,Paizs, Csaba,Irimie, Florin-Dan,Kanerva, Liisa T.
, p. 142 - 150 (2013/04/10)
Eight racemic 1-(furan-2-yl)ethanols were prepared from the corresponding carbonyl compounds for enantioselective acylation studies, and seven of them were used in preparative-scale kinetic resolutions with Candida antarctica lipase B (Novozym 435) and vinyl acetate in dried diisopropyl ether. Mechanism-based competition between the (R)-acetate (enzymatic acylation product), vinyl acetate (added acylating reagent), and acetic acid (enzymatic hydrolysis product) toward CAL-B, together with the residual water of the lipase were shown to be potential reasons for side reactions, which affected the course of the kinetic resolution of 1-[5-(2-chlorophenyl) and (4-bromophenyl)furan-2-yl]ethanols. Clear effects were not observed with the other alcoholic substrates. Alcoholysis of the enantiomerically enriched (R)-acetates with methanol and CAL-B in diisopropyl ether was shown to be a potential method for the deprotection of the (R)-acetates and the formation of (R)-alcohols.
Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast
Trif, Maria,Kall, Noemi Hajnalka,Naghi, Mara Ana,Bencze, Laszl Csaba
, p. 177 - 183 (2012/06/30)
Baker's yeast mediated reduction of various phenylfuran-2-yl-ethanones has been studied. The influence of the reaction conditions, the type and position of the substituents, as well the presence of various additives on the enantiomeric composition of the products and the reaction yield are discussed. The absolute configuration of the reaction products was established using a retrosynthetic procedure.
