EPHEDRINE-DERIVED IMIDAZOLIDIN-2-ONES - BROAD UTILITY CHIRAL AUXILIARIES IN ASYMMETRIC-SYNTHESIS

被引：51

作者：

DREWES, SE

MALISSAR, DGS

ROOS, GHP

机构：

[1] Department of Chemistry, University of Natal, Pietermaritzburg, 3200

来源：

CHEMISCHE BERICHTE | 1993年 / 126卷 / 12期

关键词：

IMIDAZOLIDIN-2-ONE,(4R,5S)-1,5-DIMETHYL-5-PHENYL- OR CYCLOHEXYL-; (-)-EPHEDRINE; STEREOSELECTIVE ALDOL; ALKYLATION; ACYLATION;

D O I：

10.1002/cber.19931261216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The scope of the readily available (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one (4) and its 4-cyclohexyl analogue 6 as practical, efficient chiral auxiliaries has been demonstrated. The enolate chemistry of their N-acyl derivatives exhibits features which recommend their use in asymmetric synthesis. The stereoselective boron-mediated aldol as well as alkylation and acylation results are presented. The steric control benefit derived by conversion of phenyl to cyclohexyl is highlighted.

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页码：2663 / 2673

页数：11

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