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Enantioselective Copper‐Catalyzed Borylative Cyclization for the Synthesis of Quinazolinones

Quentin Dherbassy, Srimanta Manna, Chunling Shi, Watcharapon Prasitwatcharakorn, Giacomo E. M. Crisenza, Gregory J. P. Perry, David J. Procter

2021Angewandte Chemie International Edition44 citationsDOIOpen Access PDF

Abstract

Quinazolinones are common substructures in molecules of medicinal importance. We report an enantioselective copper-catalyzed borylative cyclization for the assembly of privileged pyrroloquinazolinone motifs. The reaction proceeds with high enantio- and diastereocontrol, and can deliver products containing quaternary stereocenters. The utility of the products is demonstrated through further manipulations.

Topics & Concepts

Enantioselective synthesisCopperCatalysisCombinatorial chemistryChemistryOrganic chemistryQuinazolinone synthesis and applicationsN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry Methods