Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts.
Highly enantioselective selenocyclization reactions are promoted by the combination of a new chiral squaramide catalyst, a mineral acid, and an achiral Lewis base. Mechanistic studies reveal that the enantioselectivity originates from the dynamic kinetic resolution of seleniranium ions through anion-binding catalysis.
Department of Chemistry & Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
Hu
H
Zhang
Song
S
Lin
Eric N
EN
Jacobsen
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D007700:Kinetics; D058115:Lewis Bases / Q000737:chemistry*; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
D000143:Acids; D058115:Lewis Bases; D016566:Organoselenium Compounds