Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane.
A variety of nonconjugated cis-olefins has been enantioselectively epoxidized with chiral ketones 2, and up to 92% ee has been obtained. The two prochiral faces of an olefin are likely stereodifferentiated by the relative hydrophobicity of the olefin substituents and/or allylic oxygen functionality.
Burke
Christopher P
CP
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Shi
Yian
Y
D000475:Alkenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D004852:Epoxy Compounds; D007659:Ketones; C061799:dioxirane