The intramolecular salt effect in chiral auxiliaries. Enhanced diastereoselectivity in a nitrile oxide cycloaddition via rational transition state stabilization.

被引：17

作者：

Raposo, C ^{[1
]}

Wilcox, CS ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(98)02692-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of ion pairs to control a nitrile oxide cycloaddition is demonstrated. A chiral phenylmaleimide derivative bearing an ionic group and an associated counterion provides enhanced selectivity in the cycloaddition of benzonitrile oxide. The intramolecular salt effect controls the orientation of the 1,3-dipolar reagent. The nature of the solvent is shown to be relevant in the selectivity of the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1285 / 1288

页数：4

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