Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane.
This paper describes a highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketone 2 as catalyst and Oxone as oxidant to form cis-propargyl epoxides in high ee's. The interaction between the alkyne group of the substrate and the oxazolidinone moiety of the ketone catalyst as well as the interactions between the substituents on enynes and the oxazolidinone moiety of the ketone catalyst are important for the stereodifferentiation.
Burke
Christopher P
CP
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Shi
Yian
Y
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D004852:Epoxy Compounds; C061799:dioxirane