Nucleophile-Directed Selective Transformation of cis-1-Tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine into Aziridines, Azetidines, and Benzo-Fused Dithianes, Oxathianes, Dioxanes, and (Thio)morpholines Vrije Universiteit Brussel
A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2-trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-,O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen ...