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Iridium‐Catalyzed [4+3] Cyclization of ortho ‐Tosylaminophenyl‐Substituted para ‐Quinone Methides with Vinylic Oxiranes/Vinyl Aziridines
Author(s) -
Wang Junwei,
Zhao Lin,
Li Caihong,
Zhao Lei,
Zhao Kun,
Hu Yang,
Hu Lihong
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100296
Subject(s) - chemistry , iridium , catalysis , yield (engineering) , combinatorial chemistry , base (topology) , quinone , organic chemistry , medicinal chemistry , mathematical analysis , materials science , mathematics , metallurgy
An Iridium‐catalyzed [4+3] cyclization of ortho ‐tosylaminophenyl‐substituted para ‐quinone methides with vinylic oxiranes or vinyl aziridines has been successfully developed. In the presence of [Ir(cod)Cl] 2 and a suitable base, this unprecedented cascade reaction occurs readily in good yield (up to 97%) and high diastereoselectivity (dr>20 : 1), providing a highly efficient synthetic approach to synthetically valuable seven‐membered heterocyclic frameworks.