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

被引：51

作者：

Bull, Steven D. ^{[1
]}

Davies, Stephen G. ^{[1
]}

Garner, A. Christopher ^{[1
]}

Kruchinin, Dennis ^{[1
]}

Key, Min-Suk ^{[1
]}

Roberts, Paul M. ^{[1
]}

Savory, Edward D. ^{[1
]}

Smith, Andrew D. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Organ Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 15期

关键词：

D O I：

10.1039/b605244d

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

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.

引用

页码：2945 / 2964

页数：20

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