Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution.
A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where the initial product inhibition could be efficiently circumvented.
Royal Institute of Technology, Department of Chemistry, Teknikringen 30, Stockholm, Sweden. ramstrom@kth.se.
Lei
L
Hu
Yan
Y
Zhang
Olof
O
Ramström
D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D002851:Chromatography, High Pressure Liquid; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
D013843:Thiazines; D008049:Lipase