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One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α‑Trifluoromethylated Amine Derivatives

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posted on 02.05.2014, 00:00 authored by Vinay Kumar Pandey, Pazhamalai Anbarasan
Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the α-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.