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Ag I ‐Catalyzed Reaction of Enol Diazoacetates and Imino Ethers: Synthesis of Highly Functionalized Pyrroles
Author(s) -
Dong Kuiyong,
Humeidi Ahmad,
Griffith Wendell,
Arman Hadi,
Xu Xinfang,
Doyle Michael P.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202101641
Subject(s) - enol , regioselectivity , catalysis , pyrrole , chemistry , cycloaddition , combinatorial chemistry , bond cleavage , medicinal chemistry , organic chemistry
An unprecedented Ag I ‐catalyzed efficient method for the coupling of imino ethers and enol diazoacetates through a [3+2]‐cycloaddition/C−O bond cleavage/[1,5]‐proton transfer cascade process is reported. The general class of imino ethers that includes oxazolines, benzoxazoles and benzimidates are applicable substrates for these reactions that provide direct access to fully substituted pyrroles with uniformly high chemo‐ and regioselectivity. High variability in substitution at the pyrrole 2‐, 5‐ and N‐positions characterizes this methodology that also presents an entry point for further pyrrole diversification via facile modification of resulting N‐functional pyrroles.