Rhodium‐Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine‐Type Amaryllidaceae Alkaloids. Issue 52 (21st August 2017)

• Record Type: Journal Article
• Authors: Yang, Hongjian; Hou, Shengtai; Tao, Cheng; Liu, Zhao; Wang, Chao; Cheng, Bin; Li, Yun; Zhai, Hongbin
• Is Part Of: Chemistry. Volume 23:Issue 52(2017)
• Page Start: 12930
• Page End: 12936
• Publication Date: 2017-08-21
• Subjects: alkaloids -- gold -- heterocycles -- hydroindolone -- rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201702893
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Rhodium‐catalyzed denitrogenative [3+2] cycloaddition of 1‐sulfonyl‐1, 2, 3‐triazoles with cyclic silyl dienol ethers has been developed for the synthesis of functionalized hydroindolones or their corresponding silyl ethers. The present method has been employed to construct synthetically valuable bicyclo[3.3.1]alkenone derivatives and pyrrolidine‐ring‐containing bicyclic indole compounds. As a further synthetic application, a stereoselective synthesis of 5, 11‐methanomorphanthridin‐3‐one, which shares a key skeleton with montanine‐type Amaryllidaceae alkaloids has been achieved by using this chemistry. Abstract : Rhodium‐catalyzed denitrogenative [3+2] cycloaddition of 1‐sulfonyl‐1, 2, 3‐triazoles with cyclic silyl dienol ethers has been developed for the synthesis of functionalized hydroindolones or their corresponding silyl ethers. Furthermore, the diastereoselective synthesis of the framework of montanine‐type Amaryllidaceae alkaloids has also been explored by using this chemistry.