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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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Publication details

The article was received on 11 Apr 2006, accepted on 08 Jun 2006 and first published on 03 Jul 2006


Article type: Paper
DOI: 10.1039/B605244D
Citation: Org. Biomol. Chem., 2006,4, 2945-2964
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    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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