Rearrangement of Threonine and Serine-Based N-(3-Phenylprop-2-yn-1-yl) Sulfonamides Yields Chiral Pyrrolidin-3-ones.
Clicks: 352
ID: 70143
2019
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 |
Citations
No citations found. To add a citation, contact the admin at info@scimatic.org
Comments
No comments yet. Be the first to comment on this article.