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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
Journal article   Peer reviewed

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

Jean Santamaria, Mohamed Tahar Kaddachi and Clotilde Ferroud
Tetrahedron letters, Vol.33(6), pp.781-784
04/02/1992
DOI: https://doi.org/10.1016/S0040-4039(00)77714-8

Abstract

indoloquinolizidines Pictet-Spengler cyclization Single Electron Transfer α-aminonitriles
[Display omitted] A photoinduced electron transfer process sensitized by 9,10-dicyanoanthracene (DCA), using Me 3SiCN (TMSCN) an cyanating agent, yields α-aminonitriles in the indole derivatives and analogues series. Efficient synthesis of indoloquinolizidine alkaloids through a Pictet-Spengler cyclization applied to these α-aminonitriles generated in situ is described.

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