Intramolecular arylation reactions of alkenes:: A flexible approach to chromans and tetrahydroquinoline derivatives

被引：93

作者：

Barluenga, J ^{[1
]}

Trincado, M ^{[1
]}

Rubio, E ^{[1
]}

González, JM ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33006 Oviedo, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 11期

关键词：

D O I：

10.1021/ja0397299

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal-free approach to chroman derivatives by the reaction of different allylphenyl ethers with Ipy2BF4 is described. The access to this frame, by direct cyclization of the starting materials, takes place smoothly. In addition, an unusual and selective sequence that comprises initial rearrangement and further cyclization could be accomplished, with temperature as an excellent element of control. The process can be extended to the synthesis of tetrahydroquinolines when using allylamines. Also, two cascade reactions, leading to relevant oxygen and nitrogen-containing skeletons, have been devised. Copyright © 2004 American Chemical Society.

引用

页码：3416 / 3417

页数：2

共 37 条

[1] Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes [J].