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
2006; Elsevier BV; Volume: 63; Issue: 3 Linguagem: Inglês
10.1016/j.tet.2006.10.085
ISSN1464-5416
AutoresM. José Alves, Nuno G. Azóia, A. Gil Fortes,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoCycloadditions of the glyoxylate imine 1 with 1-substituted and 1,4-disubstituted 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.
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