Trimethylsilyl cyanide as a superior trapping agent for iminium ion intermediates in the dca-sensitized photooxygenation of indole derivatives and analogues. Application to the total synthesis of some indoloquinolizidine alkaloids
摘要:
A photoinduced electron transfer process sensitized by 9,10-dicyanoanthracene (DCA), using Me3SiCN (TMSCN) as cyanating agent, yields alpha-aminonitriles in the indole derivatives and analogues series. Efficient synthesis of indoloquinolizidine alkaloids through a Pictet-Spengler cyclization applied to these alpha-aminonitriles generated in situ is described.