4.8 Article

An interrupted Corey-Chaykovsky reaction of designed azaarenium salts: synthesis of complex polycyclic spiro- and fused cyclopropanoids

期刊

CHEMICAL SCIENCE
卷 14, 期 25, 页码 6963-6969

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d3sc01578e

关键词

-

向作者/读者索取更多资源

In this study, a structured remodeling of designed pyridinium salts was achieved through an interrupted Corey-Chaykovsky reaction, leading to the synthesis of unprecedented multi-ring compounds such as vicinal bis-spirocyclic indanones and spirannulated benzocycloheptanones. By rationally combining nucleophilic sulfur ylides with electrophilic pyridinium salts, a regio- and stereoselective synthesis of new classes of cyclopropanoids was achieved. Plausible mechanistic pathways were proposed based on experimental results and control experiments.
Simultaneous dearomatizing spirannulation of pyridinium salts is still in its infancy. Here, we present an organized skeletal remodeling of designed pyridinium salts by utilizing an interrupted Corey-Chaykovsky reaction to access unprecedented and structurally intriguing molecular architectures such as the vicinal bis-spirocyclic indanones and spirannulated benzocycloheptanones. This hybrid strategy rationally merges the nucleophilic features of sulfur ylides with the electrophilic pyridinium salts to achieve the regio- and stereoselective synthesis of new classes of cyclopropanoids. The plausible mechanistic pathways were derived from experimental results and control experiments.

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。

评论

主要评分

4.8
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据