SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one.
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.
Bull
Steven D
SD
The Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, UK. steve.davies@chem.ox.ac.uk
Davies
Stephen G
SG
Garner
A Christopher
AC
Kruchinin
Dennis
D
Key
Min-Suk
MS
Roberts
Paul M
PM
Savory
Edward D
ED
Smith
Andrew D
AD
Thomson
James E
JE