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 / 7卷 / 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
收藏
页码：1039 / 1044
页数：6
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