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Enantioselective nickel-catalyzed Mizoroki–Heck cyclizations of amide electrophiles

Ana S. Bulger, Daniel J. Nasrallah, Arismel Tena Meza, Neil K. Garg

2024Chemical Science11 citationsDOIOpen Access PDF

Abstract

Amide cross-couplings that rely on C-N bond activation by transition metal catalysts have emerged as valuable synthetic tools. Despite numerous discoveries in this field, no catalytic asymmetric variants have been disclosed to date. Herein, we demonstrate the first such transformation, which is the Mizoroki-Heck cyclization of amide substrates using asymmetric nickel catalysis. This proof-of-concept study provides an entryway to complex enantioenriched polycyclic scaffolds and advances the field of amide C-N bond activation chemistry.

Topics & Concepts

ElectrophileEnantioselective synthesisAmideNickelCatalysisChemistryOrganic chemistryCombinatorial chemistryCatalytic Cross-Coupling ReactionsAdvanced Synthetic Organic ChemistryChemical synthesis and alkaloids