(S)-selective kinetic resolution and chemoenzymatic dynamic kinetic resolution of secondary alcohols.
(S)-Selective kinetic resolution was achieved through the use of a commercially available protease, which was activated with a combination of two different surfactants. The kinetic resolution (KR) process was optimized with respect to activation of the protease and to the acyl donor. The KR proved to be compatible with a range of functionalized sec-alcohols, giving good to high enantiomeric ratio values (up to >200). The enzymatic resolution was combined with a ruthenium-catalyzed racemization to give an (S)-selective dynamic kinetic resolution (DKR) of sec-alcohols. The DKR process works under very mild reaction conditions to give the corresponding esters in high yields and with excellent enantioselectivities.
Borén
Linnéa
L
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
Martín-Matute
Belén
B
Xu
Yongmei
Y
Córdova
Armando
A
Bäckvall
Jan-E
JE
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism; D013381:Subtilisins / Q000737:chemistry*
D000438:Alcohols; D012428:Ruthenium; D013381:Subtilisins