SCHEDULED MAINTENANCE:
The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.
D. M. Gill, N. A. Pegg and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 1993, 1371 DOI: 10.1039/P19930001371
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