Regio- and stereo-selective aza-Diels-Alder reaction of ethyl glyoxylate 4-methoxyphenylimine with 1,3-dienes in the presence of BF3•Et2O.: Evidence for a non-concerted mechanism
Regio- and stereo-selective aza-Diels-Alder reaction of ethyl glyoxylate 4-methoxyphenylimine with 1,3-dienes in the presence of BF3•Et2O.: Evidence for a non-concerted mechanism
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DOI：
10.1016/j.tet.2006.10.085
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发表时间：
2007-01-15
期刊：
影响因子：
2.1
通讯作者：
Fortes, A. Gil
中科院分区：
文献类型：
--
作者：
Alves, M. Jose;Azoia, Nuno G.;Fortes, A. Gil
乙醛酸亚胺1与1-取代和1,4-二取代1,3-二烯的环加成使四氢喹啉化合物4和5/15具有完全的区域控制和立体控制，除了一种异构体混合物形成的情况。根据产物的立体化学性质，提出了分步反应机理。(c) 2006 Elsevier Ltd.版权所有。
Cycloadditions of the glyoxylate imine 1 with 1-substituted and 1,4-di substituted 1,3-dienes furnished tetrahydroquinoline compounds 4 and 5/15 with total regio- and stereo-control, except for one case where a mixture of isomers was formed. A stepwise mechanism is proposed in view of the stereochemistry of the products. (c) 2006 Elsevier Ltd. All rights reserved.