Synthesis of indolidines by the 1,3-dipolar cycloaddition of azides with methylenecyclopropanes followed by cyclopropyumine rearrangement
作者:Philip C. Heidt.‡、Stephen C. Bergmeier†、WilliAm H. Pearson‡
DOI:10.1016/s0040-4039(00)97867-5
日期:1990.1
Cyclic imines 6a and 6b were obtained by the intramolecular 1,3-dipolar cycloaddition of azides with methylenecyclopropanes. Acid catalyzed rearrangement produced bicyclic (−)-enamines 7, which upon reduction provided indoilizidenes 8. A similar strategy was used for the synthesis of (−)-8a-epi-desacctoxyslaframine 16.
通过叠氮化物的分子内1,3-偶极环加成与亚甲基环丙烷获得环亚胺6a和6b。酸催化的重排产生了双环(-)-烯胺7,还原后提供了indoilizidenes 8。类似的策略被用于合成(-)-8a-epi-desacctoxyslaframine 16。