title: Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones.
abstract: The combination of Fe(OTf)(2) and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic β,β-disubstituted enones, which have been a heretofore inaccessible substrate class. The reaction provides highly enantioenriched α,β-epoxyketones (up to 92% ee) that can be further converted to functionalized β-ketoaldehydes with an all-carbon quaternary center.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Nishikawa
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; D007659:Ketones; D009942:Organometallic Compounds; D007501:Iron