Publication Type
Peer Reviewed Journal
Mandatory Citation Fields
Daly, AM,Renehan, MF,Gilheany, DG;
2001
January
Organic Letters
High enantioselectivities in an (E)-alkene epoxidation by catalytically active chromium salen complexes. Insight into the catalytic cycle
Published
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ASYMMETRIC ALKENE EPOXIDATION (SALEN)MANGANESE(III) COMPLEXES ATOM TRANSFER OLEFINS OXYGEN IODOSYLBENZENE SUBSTITUENTS MECHANISM
3
663
666
[GRAPHICS]The epoxidation of (E)-beta -methylstyrene mediated by an oxochromium salen complex yields the epoxide in 92% ee in stoichiometric mode, the highest ee yet reported for a metal-mediated epoxidation of an (E)-alkene. The effect of added donor ligands, previously substantial, has reached a ceiling with this complex. In catalytic mode a slightly reduced ee and higher yield is obtained, indicating both the presence of a second oxidation cycle and that the major oxidant reacts with its reduced form.
DOI 10.1021/ol0069406
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