A novel attractive interaction in the Diels-Alder reaction of N-protected pyrroles with allene-1,3-dicarboxylates

被引：15

作者：

Nishide, K ^{[1
]}

Ichihashi, S ^{[1
]}

Kimura, H ^{[1
]}

Katoh, T ^{[1
]}

Node, N ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Kyoto 6078414, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(01)02033-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The endo/exo selectivities of Diels-Alder reactions of N-protected pyrroles with allene-1 3-dicarboxylates were studied under Lewis acid assisted and thermal reaction conditions. A novel attractive effect between the N-protective carbonyl group of pyrrole and the ester group of allene-1,3-dicarboxylates operates to control the selectivity in the above Diels-Alder reaction. This new attractive effect to give the exo adduct is more effective than the Alder orbital effect. (C) 2001 Published by Elsevier Science Ltd.

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页码：9237 / 9240

页数：4

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