Efficient and Scalable Syntheses of 1,2-Thiaselenane-4-amine and 1,2-Thiaselenane-5-amine

The first regioselective syntheses of 1,2-thiaselenane-4-amine (TSA4) and 1,2-thiaselenane-5-amine (TSA5) are developed.Both are redox motifs with high value in chemical biology that until nowwere hindered by tedious synthesis. An aziridine intermediate and a ki-netically controlled S-acylation were leveraged for regioselective chal-cogen installations. Short, fast sequences were optimised with just oneor two chromatographic steps that cheaply deliver these motifs onscale for high throughput inhibitor screening, and thus provide a robustmethodology for assembling other selenenyl sulfides