74496-21-2Relevant articles and documents
Highly selective enzymatic kinetic resolution of primary amines at 80°C: A comparative study of carboxylic acids and their ethyl esters as acyl donors
Nechab, Malek,Azzi, Nadia,Vanthuyne, Nicolas,Bertrand, Michele,Gastaldi, Stephane,Gil, Gerard
, p. 6918 - 6923 (2008/02/11)
(Chemical Equation Presented) Optimization of the kinetic resolution of 2-amino-4-phenyl-butane was achieved at 80°C using CAL-B-catalyzed aminolysis of carboxylic acids and their ethyl esters. The reactions carried out with long chain esters and the corresponding acids as acyl donors proceeded with remarkably high enantioselectivity. The use of carboxylic acids as acylating agents led to a marked acceleration of the reaction rate compared to their ester counterparts. Laurie acid led to enantiomeric excesses superior to 99.5% for both the remaining amine and the corresponding lauramide at 50% conversion (reached in 3 h). These optimized conditions were applied to the resolution of a series of aliphatic and benzylic amines.
Amidation of amines with esters catalyzed by Candida antarctica lipase (CAL)
Yang, Bo,Zhang, Yanjun,Zhang, Shusheng,Izumi
, p. 1312 - 1316 (2007/10/03)
Candida antarctica lipase (CAL) is used to convert amines and esters into amides, especially as a chiral resoluting catalyst for the enantioselective amidation of racemic esters or racemic amines in an effort to demonstrate the ability of lipase to differentiate between enantiomeric substrates. It is a very useful synthetic method for amides. The effects of substrate modification on the yield and enantiomeric excess (ee) are studied. The R-enantiomer will react faster for racemic mixture of amine in which the amino group attaches directly to the chiral carbon, and the same for racemic mixture of ester in which the carbonyl group attaches directly to the chiral carbon. The enantioselectivity of CAL is complicated for the amidation of racemic mixture of amine with racemic mixture of ester.
