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A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem -bis(triflyl)ated cyclopenta[ b ]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[ b ]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.

Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines