Lipase-catalyzed kinetic resolution of beta-borylated carboxylic esters
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
05/11/2013
05/11/2013
2012
|
| Resumo |
The kinetic resolution of chiral beta-borylated carboxylic esters via lipase-catalyzed hydrolysis and transesterification reactions was studied. The enantioselective hydrolysis catalyzed by CAL-B furnished the beta-borylated carboxylic acid with reasonable enantiomeric excess (62% ee), while both methyl and ethyl beta-borylated carboxylic esters were recovered with excellent ee (>99%). Meanwhile, the transesterification reaction of beta-borylated carboxylic esters and several alcohols, catalyzed by CAL-B, only indicated a high selectivity when ethanol and methyl-(beta-pinacolylboronate)-butanoate were used as substrates, which gave ethyl-(beta-pinacolylboronate)-butanoate with >99% ee. (C) 2012 Elsevier Ltd. All rights reserved. FAPESP FAPESP CNPq CNPq CAPES CAPES |
| Identificador |
TETRAHEDRON-ASYMMETRY, OXFORD, v. 23, n. 17, pp. 1294-1300, SEP 15, 2012 0957-4166 http://www.producao.usp.br/handle/BDPI/41519 10.1016/j.tetasy.2012.08.011 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD OXFORD |
| Relação |
TETRAHEDRON-ASYMMETRY |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #CROSS-COUPLING REACTION #CANDIDA-RUGOSA #ALPHA,BETA-UNSATURATED ESTERS #ASYMMETRIC REDUCTION #HYDROXY ESTERS #ACID #BORATION #ENANTIOSELECTIVITY #ESTERIFICATION #BIOCATALYSTS #CHEMISTRY, INORGANIC & NUCLEAR #CHEMISTRY, ORGANIC #CHEMISTRY, PHYSICAL |
| Tipo |
article original article publishedVersion |
