AN AM1 STUDY ON PI-FACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF 2-AZA-1,3-DIENES WITH AZODIENOPHILES

被引：0

作者：

BARLUENGA, J

SORDO, TL

SORDO, JA

FUSTERO, S

GONZALEZ, J

机构：

[1] UNIV OVIEDO, FAC QUIM, DEPT QUIM FIS & ANALIT, E-33006 OVIEDO, SPAIN

[2] UNIV VALENCIA, FAC FARM, DEPT QUIM ORGAN, E-46100 VALENCIA, SPAIN

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 1994年 / 121卷

关键词：

D O I：

暂无

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A theoretical study of the pi-facial selectivity in Diels-Alder reactions of chloro derivatives of 2-aza-1,3-dienes with azodienophiles has been carried out using the semiempirical AM1 method. Three transition structures for the model reaction of the diene 3 with the dienophile 4 were located. The Diels-Alder reaction of the non-substituted 2-aza-1,3-diene 6 with the trans-diimide was studied. All transition structures located show an important asynchronicity and the calculations reveal the presence of stereoelectronic effects. The predicted stereoselectivity is in agreement with the experimental evidence.

引用

页码：63 / 69

页数：7

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