33533-53-8Relevant articles and documents
Enzyme-mediated enantioselective hydrolysis of soluble polymer-supported carboxylates
Okudomi, Masayuki,Ageishi, Kanpei,Yamada, Tomomi,Chihara, Naoka,Nakagawa, Takuya,Mizuochi, Katsumi,Matsumoto, Kazutsugu
experimental part, p. 8060 - 8067 (2010/10/20)
The enzyme-mediated enantioselective hydrolysis of water-soluble polymer-supported carboxylates is disclosed. The representative monomethoxy poly(ethylene glycol) (MPEG, av MW 5000)-supported substrate was synthesized by immobilization of (±)-1-phenylethanol onto the modified MPEG (MPEG/NH2) through an carboxylate linker with a succinate spacer. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by lipase from Candida antarctica (Novozym 435) in a mixed solvent (hexane/buffer=9/1) at 30 °C to afford the remaining (S)-substrate and the resulting (R)-alcohol (E value>200). The products were easily separated by a simple procedure without any laborious column chromatography. The substrate was hydrolyzed with NaOH in MeOH/H2O to afford the corresponding (S)-alcohol. We also found that the structure of the spacer between the MPEG moiety and the carboxylate linker strongly affected both the reactivity and enantioselectivity, and the substrate bearing a glutarate spacer gave the best result. Our procedure was applicable for the preparation of several optically active alcohols.
EFFECT OF THE NATURE OF THE ACYLATING AGENT ON THE ASYMMETRIC ACYLATION OF ALCOHOLS
Potapov, V. M.,Dem'yanovich, V. M.,Klebnikov, V. A.,Korovina, T. G.
, p. 1095 - 1097 (2007/10/02)
During the acylation of racemic 1-phenylethanol by the action of carboxylic acid anhydrides in the presence of S-(-)-N,N-dimethyl-α-phenylethylamine the unreacted alcohol is enriched in the S isomer.Its optical purity increases with increase in the steric demands of the anhydride from 2percent for acetic anhydride to 9percent for benzoic anhydride.When carboxylic acid chlorides are used, optically active 1-phenyl-1-chloroethane and bis-1-phenylethyl ether are isolated in addition to S-(-)-1-phenylethanol.