title: Catalytic asymmetric heterodimerization of ketenes.
abstract: In this Communication we describe an unprecedented catalytic asymmetric heterodimerization of ketenes of wide substrate scope. The alkaloid-catalyzed method provides access to ketene heterodimer β-lactones and allows even two different monosubstituted ketenes to be cross-dimerized, with excellent enantioselectivity (17 examples with ≥90% ee) and excellent heterodimer regioselectivity observed in all cases.
authors.affiliation: Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, USA.
authors.forename: Ahmad A
authors.initials: AA
authors.lastname: Ibrahim
authors.forename: Divya
authors.initials: D
authors.lastname: Nalla
authors.forename: Maxwell
authors.initials: M
authors.lastname: Van Raaphorst
authors.forename: Nessan J
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D002384:Catalysis; D002621:Chemistry / Q000379:methods*; D002845:Chromatography / Q000379:methods; D002849:Chromatography, Gas / Q000379:methods; D019281:Dimerization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D008956:Models, Chemical; D055503:Protein Multimerization; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D005030:Ethylenes; D007659:Ketones; D007783:Lactones; D012997:Solvents; C008223:ketene