Effect of Lewis acid catalysis on the Diels-Alder reaction between methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoate and cyclopentadiene. A theoretical study

被引：47

作者：

Sbai, A ^{[1
]}

Branchadell, V ^{[1
]}

Ortuno, RM ^{[1
]}

Oliva, A ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA, DEPT QUIM, BELLATERRA 08193, SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo960447j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions of methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2 and (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoic acid with cyclopentadiene catalyzed by AlCl3 have been theoretically studied at the B-LYP/G-31G* level. The results obtained show that the catalyst increases both the endo/exo and syn/anti selectivity, in good qualitative agreement with the experimental observations. The origin of the selectivity and the role of the catalyst are discussed.

引用

页码：3049 / 3054

页数：6

共 49 条

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