Jian Yong, He Yu-Jie, Hu Chao, Li Xingguang, Liu Pei-Nian
Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
Shanghai Neutan Pharmaceutical Co., Ltd., Building 26, No.555 Huanqiao Road, Pudong New Area, Shanghai 201315, P. R. China.
Org Lett. 2024 Oct 11;26(40):8492-8497. doi: 10.1021/acs.orglett.4c03018. Epub 2024 Sep 27.
A novel substrate-regulated [4+1] annulation of α-imidoyl sulfoxonium ylides with diazoketones under catalyst-free conditions is described. The reaction proceeds through a coupling of sulfoxonium ylides and in situ-generated ketenes to form the key reactive zwitterionic intermediates, followed by selective formation of C-C or C-O bonds to achieve five-membered ring systems. The cascade reaction permits the direct synthesis of synthetically useful 2-indanones and 3(2)-furanones, which expands the reaction pattern of sulfoxonium ylides in annulation transformation.
本文描述了一种新型的、在无催化剂条件下α-亚胺基硫鎓叶立德与重氮酮的底物调控[4+1]环化反应。该反应通过硫鎓叶立德与原位生成的烯酮偶联形成关键的反应性两性离子中间体，随后选择性地形成碳-碳或碳-氧键以实现五元环体系。该串联反应可直接合成具有合成价值的2-茚酮和3(2)-呋喃酮，拓展了硫鎓叶立德在环化转化中的反应模式。
