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

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.
Publication status:
Published

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Publisher copy:
10.1039/b605244d

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
Organic and biomolecular chemistry
Volume:
4
Issue:
15
Pages:
2945-2964
Publication date:
2006-08-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:c59be8b7-8608-4b4b-a563-7e3e149ad557
Source identifiers:
110556
Local pid:
pubs:110556
Language:
English

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