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Paper | Special issue | Vol 76, No. 2, 2008, pp.1121-1131
Published online, 15th May, 2008
DOI: 10.3987/COM-08-S(N)69
Crystal Structure Analysis and Reactivity of N-Alkyl- and N-Acyldioxathiazinanes

Fabrice Galaud, John W. Blankenship, and William D. Lubell*

*Department of Chemistry, University of Montreal, C.P.6128, Downtown Station. Montréal, Québec, H3C 3J7, Canada

Abstract

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 and N-alkyl counterparts, and were previously suggested to be more reactive due to carbamoylation of the -NH moiety generating an electron withdrawing effect. Probing this enhanced reactivity by the synthesis and structural analysis of N-Boc- and N-PhF-dioxathiazinanes using NMR spectroscopy, X-ray diffraction, and DFT calculations, we now describe a unique, reactive twisted conformation in N-acyl dioxathiazinanes.