硫叶立德的底物导向发散环化反应：官能化双螺环戊烷和双螺环丙烷衍生物的合成
Substrate-directed divergent annulations of sulfur ylides: synthesis of functionalized bispirocyclopentane and bispirocyclopropane derivatives.
作者信息
Chen Siyi, Liang Peiyao, Cai Yilin, Zhou Liejin, Wang Shoulei
机构信息
Strait Institute of Flexible Electronics (SIFE, Future Technologies), Fujian Key Laboratory of Flexible Electronics, Fujian Normal University and Strait Laboratory of Flexible Electronics (SLoFE), Fuzhou 350117, China.
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, Jinhua 321004, China.
出版信息
Org Biomol Chem. 2024 Mar 13;22(11):2197-2202. doi: 10.1039/d4ob00146j.
Herein, an efficient, substrate-directed divergent [2 + 3]/[2 + 1] annulation of tetra-substituted oxa-dienes and allylic sulfur ylides has been successfully developed. Under precise annulation regulation, a series of functionalized bispirocyclopentane and bispirocyclopropane derivatives were synthesized in a highly stereoselective and economical manner (up to 95% yield, >20 : 1 dr or >20 : 1 /). This protocol offers the advantages of mild conditions, high chemo-, regio- and diastereoselectivity and broad substrate compatibility. In addition, the synthetic practicality of this protocol was evaluated through a scale-up preparation and a series of three-component reactions utilizing generated sulfur ylides.
在此，已成功开发出一种高效的、底物导向的四取代氧杂二烯与烯丙基硫叶立德的发散性[2 + 3]/[2 + 1]环化反应。在精确的环化调控下，以高立体选择性和经济的方式合成了一系列功能化的双螺环戊烷和双螺环丙烷衍生物（产率高达95%，非对映选择性>20:1或对映选择性>20:1）。该方法具有条件温和、化学选择性、区域选择性和非对映选择性高以及底物兼容性广等优点。此外，通过放大制备以及利用生成的硫叶立德进行的一系列三组分反应，评估了该方法的合成实用性。
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