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

doi:10.1021/acs.joc.9b02932

Paper

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

Published Dec 6, 2019 · P. Králová, M. Maloň, J. Pospíšil

The Journal of organic chemistry

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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.

Study Snapshot

This study demonstrates that pyrrolidin-3-ones can be synthesized from serine and threonine-based N-(3-phenylprop-2-yn-1-yl)-sulfonamides, yielding unexpected chiral compounds.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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Citations

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Polymer-supported allylglycine enables facile parallel synthesis of novel, pharmacologically promising compounds with fused [6 + 6] or [6 + 7] rings.

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