Rearrangement of Threonine and Serine-Based N-(3-Phenylprop-2-yn-1-yl) Sulfonamides Yields Chiral Pyrrolidin-3-ones.
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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.
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| Authors | Králová, Petra;Maloň, Michal;Pospisil, Jiri;Soural, Miroslav; |
| Journal | The Journal of organic chemistry |
| Year | 2019 |
| DOI |
10.1021/acs.joc.9b02932
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