Asymmetric epoxidation of 1,1-disubstituted terminal olefins by chiral dioxirane via a planar-like transition state.
Various 1,1-disubstituted terminal olefins have been investigated for asymmetric epoxidation using chiral ketone catalysts. Up to 88% ee has been achieved with a lactam ketone, and a planar transition state is likely to be a major reaction pathway.
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Bin
B
Wang
O Andrea
OA
Wong
Mei-Xin
MX
Zhao
Yian
Y
Shi
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000475:Alkenes; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007659:Ketones; C061799:dioxirane