New findings on the cerium(IV) ammonium nitrate catalyzed Povarov reaction:: Stereoselective synthesis of 4-alkoxy-2-aryl-1,2,3,4-tetrahydroquinoline derivatives

被引：45

作者：

Sridharan, Vellaisamy ^{[1
]}

Avendano, Carmen ^{[1
]}

Menendez, J. Carlos ^{[1
]}

机构：

[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

来源：

SYNTHESIS-STUTTGART | 2008年 / 07期

关键词：

cycloadditions; multicomponent reactions; stereoselective synthesis; Lewis acids; quinolines;

D O I：

10.1055/s-2008-1032126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cerium(IV) ammonium nitrate catalyzes the three-component, imino Diels-Alder (Povarov) reaction between anilines, aromatic aldehydes, and acyclic vinyl ethers, giving cis-4-alkoxy-2aryl-1,2,3,4-tetrahydroquinolines with almost complete diastereoselectivity. The corresponding reaction starting from cyclic vinyl ethers gave the two possible diastereomers, with the endo-compound as the major product. This stereochemical outcome is explained through a stepwise mechanism for the imino Diels-Alder reaction, and this mechanism was subsequently proved by trapping the putative oxonium intermediate in the presence of ethanol.

引用

页码：1039 / 1044

页数：6