Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.
New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic α-substituted β-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted β-lactones are produced in good yield with good to excellent selectivities (see scheme).
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA.
Daniel T
DT
Cohen
Chad C
CC
Eichman
Eric M
EM
Phillips
Emily R
ER
Zarefsky
Karl A
KA
Scheidt
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D003517:Cyclopentanes; D006571:Heterocyclic Compounds; D007783:Lactones; C030011:carbene; C116609:3-hydroxybutanal; D008697:Methane