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Applications of vinylogous mannich reactions. Concise enantiospecific total syntheses of (+)-croomine

SF Martin, KJ Barr, DW Smith…

文献索引:Martin, Stephen F.; Barr, Kenneth J.; Smith, Dudley W.; Bur, Scott K. Journal of the American Chemical Society, 1999 , vol. 121, # 30 p. 6990 - 6997

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被引用次数: 100

摘要

Because the vinylogous Mannich reaction of substituted furans with iminium ions is a useful construction in alkaloid synthesis, it is important to know what effects substituents on the two reacting partners have upon the stereoselectivity of the reaction. Toward this end, the additions of the methylated furans 9a-h to the iminium ion generated in situ from the ethoxy carbamate 10 were examined. Generally, mixtures (3-24: 1) of the threo and erythro ...