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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101641
Subject(s) - enol , pyrrole , catalysis , regioselectivity , cycloaddition , chemistry , bond cleavage , enol ether , medicinal chemistry , combinatorial chemistry , organic chemistry
Abstract 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.