{"title":"Asymmetric Synthesis of Pyrrolo[1,2-a]indoles via Bifunctional Tertiary Amine Catalyzed [3+2] Annulation of 2-Nitrovinylindoles with Azlactones","authors":"Xiao-Long He, Xiaomei Li, Song Wu, Jiachen Xie, Jiang Deng, Junyuan Yan, Wei Li, Zhiming Li, Zhouyu Wang, Shan Qian","doi":"10.1039/d4qo01557f","DOIUrl":null,"url":null,"abstract":"The chiral pyrrolo[1,2-a]indole represents a privileged stuctural motif in many natual products and pharmaceutical agents. Herein we developed an efficient [3+2] annulation of 2-nitrovinylindoles with azlactones via the cascade Michael addition and intramolecular acylation under the catalysis of bifunctioanl tertiary amine in combination with DABCO, delivering a wide range of pyrrolo[1,2-a]indoles in good yields with high diastereo- and enantioselectivities. Alternatively, 7-nitrovinylindoles are served as 4C-synthons to perform the enantioselective [4+2] annulation under the identical condition, smoothly giving the pyrrolo[3,2,1-ij]quinoline skeleton with good to high stereoselectivities. Furthermore, a novel enantio-enriched indole-based tetracyclic skeleton was facilely derived from the obtained pyrrolo[1,2-a]indoles.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01557f","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The chiral pyrrolo[1,2-a]indole represents a privileged stuctural motif in many natual products and pharmaceutical agents. Herein we developed an efficient [3+2] annulation of 2-nitrovinylindoles with azlactones via the cascade Michael addition and intramolecular acylation under the catalysis of bifunctioanl tertiary amine in combination with DABCO, delivering a wide range of pyrrolo[1,2-a]indoles in good yields with high diastereo- and enantioselectivities. Alternatively, 7-nitrovinylindoles are served as 4C-synthons to perform the enantioselective [4+2] annulation under the identical condition, smoothly giving the pyrrolo[3,2,1-ij]quinoline skeleton with good to high stereoselectivities. Furthermore, a novel enantio-enriched indole-based tetracyclic skeleton was facilely derived from the obtained pyrrolo[1,2-a]indoles.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.