Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution

C Paizs, P Tähtinen, K Lundell, L Poppe, FD Irimie…

Index: Paizs, Csaba; Taehtinen, Petri; Lundell, Katri; Poppe, Laszlo; Irimie, Florin-Dan; Kanerva, Liisa T. Tetrahedron Asymmetry, 2003 , vol. 14, # 13 p. 1895 - 1904

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Citation Number: 45

Abstract

A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of ...