Activation of the dienophilicity of indoles in normal electron demand [4+2] cycloadditions under high pressure

被引：63

作者：

Chataigner, I

Hess, E

Toupet, L

Piettre, SR

机构：

[1] Univ Rouen, IRCOF, UMR 6014 CNRS, Lab Fonct Azotees & Oxygenees Complexes, F-76821 Mt St Aignan, France

[2] Univ Rennes 1, UMR 6626 CNRS, F-35042 Rennes, France

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 04期

关键词：

D O I：

10.1021/ol0067989

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Activation by either high pressure or a combination of Lewis acid catalysis and high pressure allows indole derivatives to behave as dienophiles in [4 + 2] cycloaddition reactions under mild conditions. The biactivation mode has the highest impact on the stereoselectivity of the reaction. The cycloadducts resulting from these reactions are characterized by boat shape conformations that bear well-defined orthogonal planes.

引用

页码：515 / 518

页数：4

共 25 条

[1]

ABEN RWM, 1992, HIGH PRESSURE RES, V11, P167

[2]

BACKVALL JE, 1990, J ORG CHEM, V55, P4528

[3] INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - 5H-PYRIDAZINO[4,5-B]INDOLES AS CYCLOADDUCTS WITH 3,6-DICARBOMETHOXY-1,2,4,5-TETRAZINE [J].