title: SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one.
abstract: The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.
authors.affiliation: The Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, UK. steve.davies@chem.ox.ac.uk
authors.forename: Steven D
authors.initials: SD
authors.lastname: Bull
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: A Christopher
authors.initials: AC
authors.lastname: Garner
authors.forename: Dennis
authors.initials: D
authors.lastname: Kruchinin
authors.forename: Min-Suk
authors.initials: MS
authors.lastname: Key
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Edward D
authors.initials: ED
authors.lastname: Savory
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson