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

Kuiyong Dong; Ahmad Humeidi; Wendell Griffith; Hadi Arman; Xinfang Xu; Michael P Doyle

doi:10.1002/anie.202101641

Ag^I -Catalyzed Reaction of Enol Diazoacetates and Imino Ethers: Synthesis of Highly Functionalized Pyrroles

Angew Chem Int Ed Engl. 2021 Jun 7;60(24):13394-13400. doi: 10.1002/anie.202101641. Epub 2021 May 6.

Authors

Kuiyong Dong¹, Ahmad Humeidi¹, Wendell Griffith¹, Hadi Arman¹, Xinfang Xu², Michael P Doyle¹

Affiliations

¹ Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249, USA.
² Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.

PMID: 33831277
DOI: 10.1002/anie.202101641

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.

Keywords: C−O cleavage; [3+2]-cycloaddition; enodiazo compounds; imino ether; pyrroles.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.