Crystal Structure Analysis and Reactivity of N-Alkyl- and N-Acyldioxathiazinanes

• DOI: 10.3987/com-08-s(n)69
• Publication Date: 2009-02-17T07:39:12Z
• Authors: William D. Lubell; Fabrice Galaud; John W. Blankenship
• Keywords: Reactivity; Moiety

Cyclic sulfamidates have served as reactive electrophiles for the synthesis of various products, including alkaloids, substituted amines, amino acids and lactams.N-Acyl dioxathiazinanes exhibit enhanced reactivity relative to their unsubstituted N-alkyl counterparts, were previously suggested be more due carbamoylation -NH moiety generating an electron withdrawing effect.Probing this by structural analysis N-Boc-and N-PhF-dioxathiazinanes using NMR spectroscopy, X-ray diffraction, DFT calculations, we now describe a unique, twisted conformation in N-acyl dioxathiazinanes.