title: Alkali metal counterion control of enolate protonation stereoselectivity.
abstract: [reaction: see text] Generation of the lithium salt of the norbornenol shown (M = H) followed by quenching with aqueous NH(4)Cl solution gives predominantly the beta-epimeric ketone 6. Similar production of the potassium alkoxide leads instead to the alpha-epimer (99:1). These results reveal the potential importance of alkali metal counterions as stereocontrol elements.
authors.affiliation: Evans Chemical Laboratories, The Ohio State University, Columbus, 43210, USA.
authors.forename: Yang
authors.initials: Y
authors.lastname: Hu
authors.forename: Raynauld L
authors.initials: RL
authors.lastname: Bishop
authors.forename: Andreas
authors.initials: A
authors.lastname: Luxenburger
authors.forename: Shuzhi
authors.initials: S
authors.lastname: Dong
authors.forename: Leo A
authors.initials: LA
authors.lastname: Paquette
mesh_terms: D000643:Ammonium Chloride / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D008672:Metals, Alkali / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011522:Protons; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D007659:Ketones; D008672:Metals, Alkali; D009942:Organometallic Compounds; D011522:Protons; D000643:Ammonium Chloride; D014867:Water; D008094:Lithium