2013•Chemistry - A European JournalRequires access
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
Sara Kenis, Matthias D’hooghe, Guido Verniest, Maaike Reybroeck, Tuyet Anh Dang Thi, Chinh Pham The, Tham Thi Pham, Karl W. Törnroos, Nguyen Van Tuyen, Norbert De Kimpe
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Abstract
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 nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.