Dynamic kinetic resolution of benzoins by lipase-metal combo catalysis.
The synthesis of some noncommercial racemic 1,2-diaryl-2-hydroxyethanones (benzoins) is described, optimizing the previously reported methodologies. In a further step, the kinetic resolution of these substrates is reported, obtaining conversions of around 50% and ee(p) higher than 99% in very short reaction times. As enzymatic catalyst, after screening of several enzymes, the lipase TL (from Pseudomonas stutzeri) was the most efficient, working in an organic solvent with a very low log P value, such as THF. Finally, the dynamic-kinetic resolution of different benzoins using a lipase-ruthenium-catalyzed transesterification in organic solvents is described for the first time, obtaining conversions up to 90% maintaining the excellent enantioselectivity in all cases.
Hoyos
Pilar
P
Grupo de Biotransformaciones, Dpto Química Organica y Farmacéutica, Facultad Farmacia, Universidad Complutense, Plaza Ramón y Cajal s/n, E-28040 Madrid, Spain.
Fernández
María
M
Sinisterra
José Vicente
JV
Alcántara
Andrés R
AR
D001573:Benzoin / Q000138:chemical synthesis* / Q000302:isolation & purification*; D002384:Catalysis; D004951:Esterification; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D012997:Solvents
D008670:Metals; D012997:Solvents; D012428:Ruthenium; D008049:Lipase; D001573:Benzoin