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Issue 15, 2006
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SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

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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.

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

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Supplementary files

Article information


Submitted
11 Apr 2006
Accepted
08 Jun 2006
First published
03 Jul 2006

Org. Biomol. Chem., 2006,4, 2945-2964
Article type
Paper

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

S. D. Bull, S. G. Davies, A. C. Garner, D. Kruchinin, M. Key, P. M. Roberts, E. D. Savory, A. D. Smith and J. E. Thomson, Org. Biomol. Chem., 2006, 4, 2945
DOI: 10.1039/B605244D

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