title: Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation.
abstract: Attempts to reproduce eight, putative, enantioselective dibromination and chlorohydroxylation reactions from oft-cited literature studies are described. The reactions were performed with full fidelity to the original report wherever possible. Analysis of the enantiomeric composition was performed by chiral stationary phase HPLC or SFC (CSP-HPLC or CSP-SFC), as opposed to the original report, which used chiral shift reagent NMR spectroscopy. After careful study, the reported levels of enantioselectivity were found to be incorrect. Possible explanations for the false positive results are discussed.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
authors.forename: Nessa
authors.initials: N
authors.lastname: Carson
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated