Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应  

Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines

作　　者：孙李星 孙婷婷 王海清 吴淑芳 王小烨 刘天雅 张宇辰 Sun Lixing;Sun Tingting;Wang Haiqing;Wu Shufang;Wang Xiaoye;Liu Tianya;Zhang Yuchen(School of Chemistry and Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116;Department of Anesthesiology,The Affiliated Hospital of Xuzhou Medical University,Xuzhou,Jiangsu 221004;Key Laboratory of Anesthesiology of Jiangsu Province,Xuzhou Medical University,Xuzhou,Jiangsu 221004)

机构地区：[1]江苏师范大学化学与材料科学学院,江苏徐州221116 [2]徐州医科大学附属医院麻醉科,江苏徐州221004 [3]徐州医科大学江苏省麻醉学重点实验室,江苏徐州221004

出　　处：《有机化学》2023年第6期2178-2188,共11页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.22101103);江苏省自然科学基金(No.BK20201018);江苏省高层次创新创业人才引进、徐州市科技计划(No.KC21021);江苏省大学生创新(No.202110320041Z)资助项目。

摘　　要：通过Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应,以中等至良好的收率、极好的非对映选择性,合成了具有潜在抗肿瘤活性的吲哚衍生哌啶类化合物.该工作解决了3-烷基-2-吲哚烯参与的[2+4]环化反应中的挑战性问题,丰富了3-烷基-2-吲哚烯化学的研究内容.此外,该反应为高原子经济性合成含吲哚母核的哌啶衍生物提供了新方法.A Lewis acid-catalyzed [2+4] cyclization of 3-alkyl-2-vinylindoles with α,β-unsaturated N-sulfonyl ketimines was established,and indole-containing piperidines with potential antitumor activity were synthesized in moderate to good yields(up to 95% yield) and generally excellent diastereoselectivities(up to95∶5 dr).This work has confronted the challenges in exploring the [2+4] cyclization of 3-alkyl-2-vinylindoles,which will enrich the chemistry of 3-alkyl-2-vinylindoles.In addition,this approach provides an atom-economic method for the synthesis of indole-containing piperidines.

关 键 词：3-烷基-2-吲哚烯 α β-不饱和N-磺酰基亚胺 [2+4]环化反应 吲哚衍生物 

分 类 号：O621.251[理学—有机化学]