N-(3-Phenylprop-2-yn-1-yl)-sulfonamides derived from serine and threonine were synthesized using solid-phase synthesis and subjected to reaction with trimethylsilyl trifluoromethanesulfonate (TMSOTf). In contrast to the previously reported formation of 1,4-oxazepanes, this reaction afforded pyrrolidin-3-ones. A mechanistic explanation for this unexpected outcome is proposed, and the limitations and scope of the rearrangement are outlined.

Department of Organic Chemistry Faculty of Science Palacký University Tr 17 Listopadu 12 771 46 Olomouc Czech Republic

Institute of Molecular and Translational Medicine Faculty of Medicine and Dentistry Palacký University Hněvotínská 5 779 00 Olomouc Czech Republic

JEOL Limited JEOL House Silver Court Watchmead Welwyn Garden City AL7 1LT Hertfordshire United Kingdom

Laboratory of Growth Regulators The Czech Academy of Sciences Institute of Experimental Botany and Palacký University Šlechtitelů 27 78371 Olomouc Czech Republic

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$a Rearrangement of Threonine- and Serine-Based N-(3-Phenylprop-2-yn-1-yl) Sulfonamides Yields Chiral Pyrrolidin-3-ones / $c P. Králová, M. Maloň, J. Pospíšil, M. Soural

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