WEKO3
インデックスリンク
アイテム
Skeletal reorganization divergence of N-sulfonyl ynamides
https://gifu-pu.repo.nii.ac.jp/records/14236
https://gifu-pu.repo.nii.ac.jp/records/1423691c2f575-c5e3-4b3b-ab04-65fc85c9c01a
| Item type | 研究室原著論文(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2021-03-03 | |||||
| タイトル | ||||||
| タイトル | Skeletal reorganization divergence of N-sulfonyl ynamides | |||||
| 言語 | en | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 抄録 | ||||||
| 値 | Skeletal reorganization is a type of intriguing processes because of their interesting mechanism, high atom-economy and synthetic versatility. Herein, we describe an unusual, divergent skeletal reorganization of N-sulfonyl ynamides. Upon treatment with lithium diisopropylamine (LDA), N-sulfonyl ynamides undergo a skeletal reorganization to deliver thiete sulfones, while the additional use of 1,3-dimethyl-tetrahydropyrimidin-2(1H)-one (DMPU) shifts the process to furnish propargyl sulfonamides. This skeletal reorganization divergence features broad substrate scope and scalability. Mechanistically, experimental and computational studies reveal that these processes may initiate from a lithiation/4-exo-dig cyclization cascade, and the following ligand-dependent 1,3-sulfonyl migration or β-elimination would control the chemodivergence. This protocol additionally provides a facile access to a variety of privileged molecules from easily accessible ynamides. | |||||
| 書誌情報 |
en : Nature Communications 巻 11, 号 1, 発行日 2020-11-06 |
|||||
| DOI | ||||||
| 値 | 10.1038/s41467-020-19467-5 | |||||
