Stereoselective intramolecular Diels-Alder reactions of .ALPHA.,.BETA.-unsaturated amides using internal coordination of metal salts.
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The intramolecular Diels-Alder reactions between acyclic dienes and α,β-unsaturated amides utilizing the internal coordination of the metal salts have been studied in detail. When the magnesium salts of <I>N</I>-(<I>trans</I>, <I>trans</I>-2,4-alkadienyl)-<I>N</I>-(2-hydroxyphenyl)acrylamide derivatives are employed, the intramolecular Diels-Alder reactions are remarkably accelerated and the corresponding cycloadducts are obtained in high yields with isomeric ratios (<I>exo</I>-adducts: <I>endo</I>-adducts) of about 3 : 2. And the same reactions of <I>N</I>(<I>trans</I>, <I>trans</I>-2,4-alkadienyl)-<I>N</I>-(2-hydroxyphenyl)-1-cyclopentenecarboxamide afford predominantly (60 : 40 to 85 : 15 selectivity) <I>trans</I>-fused cycloadducts (<I>exo</I>-adducts) in good yields.
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