Lipase-catalyzed highly enantioselective kinetic resolution of boron-containing chiral alcohols.
The first application of enzymes as catalysts to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses (up to >99%) of both remaining substrates and acetylated product were obtained.
Andrade
Leandro H
LH
Institute of Chemistry, University of Sao Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-900, Sao Paulo, SP, Brazil. leandroh@iq.usp.br
Barcellos
Thiago
T
D000438:Alcohols / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D001896:Boron Compounds; D008049:Lipase