Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.
This paper describes a new class of chiral oxazolidinone ketone catalyst for asymmetric epoxidation. High ee values have been obtained for a number of cyclic and acyclic cis-olefins. The epoxidation was stereospecific with no isomerization observed in the epoxidation of acyclic systems. Encouragingly high ee values have also been obtained for a number of terminal olefins. Mechanistic studies show that electronic interactions play an important role in stereodifferentiation.
Tian
Hongqi
H
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
She
Xuegong
X
Yu
Hongwu
H
Shu
Lianhe
L
Shi
Yian
Y
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000475:Alkenes; D004852:Epoxy Compounds; D007659:Ketones