The Birch reduction-alkylation coupled to the desymmetrizing Mizoroki-Heck reaction is a novel synthetic tool to form fused tricyclic ring systems with a quaternary stereocenter from inexpensive and easily available starting materials. We have developed the first example of creating phenanthridinone analogs using the enantioselective intramolecular Ni-catalyzed Mizoroki-Heck reaction of 1,4-diene systems tethered to aryl halides in good to excellent yields. We made important advances in reaction optimization, mechanistic studies and the development of a more enantioselective process. The sustainability, high efficiency and low price of nickel catalysts make this work a very attractive alternative to the palladium-version.

Nickel-catalyzed enantioselective synthesis of new phenanthridinone analogs with quaternary carbon stereocenters using the Birch-Heck reaction sequence

ACS Spring 2022

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