Iridium-Catalyzed Aza-Spirocyclization of Indole-Tethered Amides: An Interrupted Pictet–Spengler Reaction
作者:Pablo Gabriel、Alex W. Gregory、Darren J. Dixon
DOI:10.1021/acs.orglett.9b02194
日期:2019.9.6
A mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska's complex with tetramethyldisiloxane as the terminal reductant allowed iminium ion formation, before a diastereoselective 5-endo-trig spirocyclization of the tethered
描述了轻度还原吲哚连接的酰胺和内酰胺的螺环化,以有效和选择性地合成氮杂-螺环吲哚啉产物。Vaska络合物与四甲基二硅氧烷作为末端还原剂对叔酰胺或内酰胺的催化还原活化作用可引发亚胺离子的形成,然后引发栓系吲哚部分的非对映选择性5-内-trig螺环化。末端还原以整体高度化学选择性和非对映选择性的一锅法提供了氮杂螺并吲哚啉产品。