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