An Interrupted [4+3] Cycloaddition Reaction: A Hydride Shift (Ene Reaction) Intervenes

被引：46

作者：

Harmata, Michael ^{[1
]}

Huang, Chaofeng ^{[1
]}

Rooshenas, Parham ^{[2
]}

Schreiner, Peter R. ^{[2
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

[2] Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 45期

基金：

美国国家科学基金会;

关键词：

carbocations; cycloaddition; ene reaction; hydrogen shift; oxyallylic cations;

D O I：

10.1002/anie.200803487

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The road less traveled does indeed make all the difference. The reaction of oxyallylic cations with cyclopentadiene usually yields a [4+3] cycloadduct. Instead, a hydride shift can supersede this cycloadditon process and proceed in synthetically useful yields (see scheme). Computational analyses suggest that substantial electronic effects influence the road" taken by the oxyallylic cation. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA."

引用

页码：8696 / 8699

页数：4

共 51 条

[21] A new approach to the Nazarov reaction via sequential electrocyclic ring opening and ring closure [J].