221878-52-0Relevant articles and documents
Improvement of enantioselectivity in kinetic resolution of a primary alcohol through lipase-catalyzed transesterification by using a chiral acyl donor
Hirose, Keiji,Naka, Hiroyuki,Yano, Masashi,Ohashi, Sozaburo,Naemura, Koichiro,Tobe, Yoshito
, p. 1199 - 1210 (2000)
The enantioselectivity of the kinetic resolution of a primary alcohol which has a chiral center at the β-position of the hydroxyl group was substantially improved by employing a racemic mixture of a chiral acyl donor for enantioselective transesterification catalyzed by a lipase. The combination of the lipase, solvent, and acyl donor was also effective for the enantioselectivity. In addition, the important effect of the chirality of an acyl donor on kinetic resolution was investigated by using enantiomerically pure acyl donors. Here we demonstrate the effective kinetic resolution (E=98) of a primary alcohol, 2-phenyl-1-propanol, by using a racemic mixture of a chiral acyl donor, vinyl 3-phenylbutanoate. Copyright (C) 2000 Elsevier Science Ltd.
Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy
Humphrey, Cara E.,Turner, Nicholas J.,Easson, Morag A. M.,Flitsch, Sabine L.,Ulijn, Rein V.
, p. 13952 - 13953 (2007/10/03)
The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright