Stereoselective formation of activated cyclopropanes with pyridinium ylides bearing a (-)-8-phenylmenthyl group as the chiral auxiliary

被引：47

作者：

Kojima, S ^{[1
]}

Fujitomo, K ^{[1
]}

Shinohara, Y ^{[1
]}

Shimizu, M ^{[1
]}

Ohkata, K ^{[1
]}

机构：

[1] Hiroshima Univ, Grad Sch Sci, Dept Chem, Higashihiroshima 7398526, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 50期

关键词：

pyridinium ylide; activated cyclopropane; 8-phenylmenthyl; diastereoselective;

D O I：

10.1016/S0040-4039(00)01743-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of various mono-substituted methylidenemalononitriles with (-)-8-phenylmenthyl alpha -pyridiniumacetate in the presence of base afforded the corresponding dicyanocyclopropane compounds with exclusive trans-selectivity and good diastereoselectivity (up to 86.14). The stereochemistry of the major products were determined to be of 1R configuration by X-ray structural analysis of the crystalline tuans -2,2-dicyano-3-(4-pyridyl)cyclopropanecarboxylate. The geometric and diastereofacial selectivities were rationalized assuming anti-periplanar approach in the open-chain model, followed by epimerization and then cyclization to give the cyclopropane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9847 / 9851

页数：5

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