AgI-Catalyzed Reaction of Enol Diazoacetates and Imino Ethers: Synthesis of Highly Functionalized Pyrroles

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.

Automated summary

An unprecedented Ag-catalyzed efficient method for the coupling of imino ethers and enol diazoacetates through a cascade process is reported, providing direct access to fully substituted pyrroles with high chemo- and regioselectivity. The methodology allows for high variability in substitution at the pyrrole positions, presenting an entry point for further pyrrole diversification via facile modification of resulting N-functional pyrroles.