Dynamic kinetic resolution of phenylglycine esters via lipase-catalysed ammonolysis

被引：62

作者：

Wegman, MA ^{[1
]}

Hacking, MAPJ ^{[1
]}

Rops, J ^{[1
]}

Pereira, P ^{[1
]}

van Rantwijk, F ^{[1
]}

Sheldon, RA ^{[1
]}

机构：

[1] Delft Univ Technol, Organ Chem & Catalysis Lab, NL-2628 BL Delft, Netherlands

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(99)00143-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Ammonolysis of D,L-phenylglycine methyl ester catalysed by Novozym 435 at 40 degrees C in tert-butyl alcohol gave D-phenylglycine amide in 78% ee at 46% conversion, corresponding to an enantiomeric ratio (E) of 16. Lowering the temperature improved the enantioselectivity (E=52 at -20 degrees C). Combination of ammonolysis with pyridoxal-catalysed in situ racemisation of the unconverted ester (dynamic kinetic resolution), at -20 degrees C, gave D-phenylglycine amide with 88% ee at 85% conversion. The amide racemised much slower than the ester at this low temperature. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1739 / 1750

页数：12

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