title: An NMR method for assigning relative stereochemistry to beta-hydroxy ketones deriving from aldol reactions of methyl ketones.
abstract: We describe a simple 1H NMR analysis that permits the stereochemistry of beta-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the alpha-methylene unit of the beta-hydroxy ketone in the 1H NMR spectra. This method has been verified by application to a wide range of beta-hydroxy ketones deriving from aldol reactions of chiral aldehydes with a variety of chiral and achiral methyl ketone enolates (see Tables 1 and 2). The stereochemistry of 54 of these compounds have been assigned by rigorous chemical methods.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Bannister
authors.forename: Michael D
authors.initials: MD
authors.lastname: Wendt
authors.forename: Michael S
authors.initials: MS
authors.lastname: VanNieuwenhze
authors.forename: Darin J
authors.initials: DJ
authors.lastname: Gustin
authors.forename: Garrett J
authors.initials: GJ
authors.lastname: Dilley
authors.forename: Gregory C
authors.initials: GC
authors.lastname: Lane
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
authors.forename: William J
authors.initials: WJ
authors.lastname: Smith
mesh_terms: D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D008697:Methane