期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 11, 页码 7045-7059出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00403
关键词
-
资金
- National Key Research and Development Program of China [2017YFD0201404]
- National Natural Science Foundation of China [21873051]
- Natural Science Foundation of Tianjin City [17JCZDJC37300]
- Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
We reported a novel two-step stereoselective synthesis of functionalized pyrrolidines from homopropargylic sulfonamides and nucleophiles via an isolable N,O-acetal intermediates. This reaction features mild conditions and good scope of substrates. In addition, the use of hexafluoroisopropanol, acting as a solvent, an additive, a weak nucleophile, and a good leaving group, is pivotal to the success of the method. Moreover, reactions of chiral homopropargylic sulfonamides afford only 2,5-cis-disubstituted pyrrolidines with high diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to >99% ee). The overall reaction constitutes a formal 1,1-bifunctionalization of terminal alkynes, which has hitherto been reported only rarely. Additionally, this method provides efficient access to pharmaceutical intermediate and to carry out postmodification of natural products.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据