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Rhodium‐Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine‐Type Amaryllidaceae Alkaloids
Author(s) -
Yang Hongjian,
Hou Shengtai,
Tao Cheng,
Liu Zhao,
Wang Chao,
Cheng Bin,
Li Yun,
Zhai Hongbin
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702893
Subject(s) - cycloaddition , amaryllidaceae alkaloids , chemistry , indole test , pyrrolidine , bicyclic molecule , silylation , rhodium , stereoselectivity , enantioselective synthesis , catalysis , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , alkaloid
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.