Highly selective enzymatic kinetic resolution of primary amines at 80 degrees C: a comparative study of carboxylic acids and their ethyl esters as acyl donors.
Optimization of the kinetic resolution of 2-amino-4-phenyl-butane was achieved at 80 degrees 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. Lauric 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.
Laboratoire de Stéréochimie Dynamique et Chiralité, UMR 6180, Chirotechnologies: Catalyse et Biocatalyse Université Paul Cézanne, Aix-Marseille III, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France.
Malek
M
Nechab
Nadia
N
Azzi
Nicolas
N
Vanthuyne
Michèle
M
Bertrand
Stéphane
S
Gastaldi
Gérard
G
Gil
D000588:Amines / Q000737:chemistry* / Q000378:metabolism*; D002264:Carboxylic Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005656:Fungal Proteins; D006536:Heptanes / Q000737:chemistry; D007700:Kinetics; D007850:Lauric Acids / Q000737:chemistry; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D013696:Temperature
D000588:Amines; D002264:Carboxylic Acids; D004952:Esters; D005656:Fungal Proteins; D006536:Heptanes; D007850:Lauric Acids; C030358:lauric acid; D008049:Lipase; C431349:lipase B, Candida antarctica