Omega-transaminases as efficient biocatalysts to obtain novel chiral selenium-amine ligands for Pd-catalysis.
Omega-transaminases have been evaluated as biocatalysts in the reductive amination of organoselenium acetophenones to the corresponding amines, and in the kinetic resolution of racemic organoselenium amines. Kinetic resolution proved to be more efficient than the asymmetric reductive amination. By using these methodologies we were able to obtain both amine enantiomers in high enantiomeric excess (up to 99%). Derivatives of the obtained optically pure o-selenium 1-phenylethyl amine were evaluated as ligands in the palladium-catalyzed asymmetric alkylation, giving the alkylated product in up to 99% ee.
Andrade
Leandro H
LH
Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-900, São Paulo, SP, Brazil. leandroh@iq.usp.br
Silva
Alexandre V
AV
Milani
Priscila
P
Koszelewski
Dominik
D
Kroutil
Wolfgang
W
D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D008024:Ligands; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism; D000637:Transaminases / Q000737:chemistry / Q000378:metabolism*
D000588:Amines; D004952:Esters; D008024:Ligands; D016566:Organoselenium Compounds; D000637:Transaminases; D012643:Selenium