Tandem cycloaddition chemistry of nitroalkenes: Preparative and theoretical studies on the stereochemical course of [3+2] cycloaddition of cyclic nitronates

被引：40

作者：

Denmark, SE ^{[1
]}

Seierstad, M ^{[1
]}

Herbert, B ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 03期

关键词：

D O I：

10.1021/jo9818374

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular [3 + 2] cycloadditions between two cyclic nitronates and a series of dipolarophiles are examined. High facial selectivity is observed in all cases and is analyzed with the aid of ab initio transition structure calculations. Monosubstituted dipolarophiles reacted with exclusive regiocontrol. Disubstituted dipolarophiles reacted with varying degrees of regiocontrol, which was dependent on the substituent. A theoretical approach for predicting regioselectivity is discussed. fro selectivity was generally favored due to steric effects, and was especially high with cis-disubstituted dipolarophiles.

引用

页码：884 / 901

页数：18

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