Rearrangement of Threonine and Serine-Based N-(3-Phenylprop-2-yn-1-yl) Sulfonamides Yields Chiral Pyrrolidin-3-ones.

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ID: 70143
2019
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Abstract
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 trifluoro-methanesulfonate (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.
Reference Key
krlov2019rearrangementthe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Králová, Petra;Maloň, Michal;Pospisil, Jiri;Soural, Miroslav;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b02932
URL
Keywords
synthesis anticancer benzenesulfonamides benzofurans carbonic anhydrases

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