Dearomative Diallylation of N-Acylindoles Mediated by FeCl3

Three-dimensional indolines possessing two contiguous-stereogenic centers were obtained stereoselectively via the FeCl3-mediated dearomative introduction of two allyl groups to N-acylindoles with allyltrimethylsilane. Synthetic transformations allowed obtention of trans-tetrahydrocarbazoles and an aza[4.4.3]propellane scaffold by RCM. Selective hydration of one of the allyl groups was also achieved.