BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS

被引：14

作者：

DAVIES, SG

EVANS, GB

PEARCE, S

机构：

[1] The Dyson Perrins Laboratory, University of Oxford, Oxford, OX1 3QY, South Parks Road

来源：

TETRAHEDRON | 1994年 / 50卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)90480-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The boron enolates of three new homochiral C-2 symmetric 1,3-diacylimidazolidin-2-ones prepared from natural tartaric acid undergo highly diastereoselective aldol and alkylation reactions. Cleavage of these diastereomerically pure, adducts gives homochiral (IR,2S)-1-phenyl-2-methylpropane-1,3-diol and (2R,3R)-3-hydroxy-3-phenyl-2-methylpropanoic acid and (2S)-3-phenyl-2-methylpropan-1-ol (>92% ee).. One of these auxiliaries, 4,5-dimethylimidazolidin-2-one, has the lowest effective molecular weight of any previously reported chiral auxiliary.

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页码：7521 / 7534

页数：14

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