SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one.

Journal article

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: Bull, S; Davies, S; Garner, A; Kruchinin, D; Key, MS

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 4
• Issue: 15
• Pages: 2945-2964
• Publication date: 2006-08-01
• DOI: 10.1039/b605244d
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English