Mason D Hamilton

West Virginia University

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Trina Perrone

West Virginia University

Brian V. Popp

West Virginia University

Brian Popp

Popp Brian

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West Virginia University

Morgantown High School

Rice University

University of Wisconsin–Madison

Instituto Venezolano de Investigaciones Científicas

Simón Bolívar University

Universidad Nacional Experimental Simón Rodríguez

Institut de Biologie Moléculaire et Cellulaire

Centre National de la Recherche Scientifique

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New methodology to controlling regioselectivity utilizing a copper-catalyzed boracarboxylation

Mason D Hamilton Trina Perrone Popp Brian

Scope of the Reaction The Asymmetric Allylic Alkylation (AAA) ReactionThe asymmetric allylic alkylation (AAA) reaction lies amongst the most powerful strategies for the catalytic construction of C-C bonds in stereoselective manner. 2 However, these transformations are mainly restricted to the use of stabilized or acidic C-nucleophiles, such as alkali-metal salts, active methylene compounds or enolates.Conversely, the use of non-acidic or non-stabilized nucleophiles remains largely underdeveloped, being specially elusive in chiral Lewis-base catalyzed AAAs.

10.1021/scimeetings.0c00822

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Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3‐Diarylpropionic Acids

Advanced Synthesis & Catalysis (2024)

Mason D Hamilton Trina Perrone Brian V. Popp

Abstract A stepwise copper‐catalyzed boracarboxylation then palladium‐catalyzed Suzuki‐Miyaura cross‐coupling methodology was developed to access 2,3‐diarylpropionic acid derivatives regioselectively by pre‐setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in three steps (31% overall yield) from commercially available 4‐ tert ‐butylstyrene.

Coupling reaction

10.1002/adsc.202400952

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Regioselective Preparation of Hetero-2,3-Diarylpropionic Acids

Mason D Hamilton Trina Perrone Brian V. Popp

A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the first catalytic reaction. This method provides a single regioisomer compared to the traditional hydrocarboxylation strategies that afford both regioisomers. Pharmaceutical potential was demonstrated in synthesizing a glucagon receptor antagonist drug in 3-steps (31% overall yield) from the commercially available 4-tert-butylstyrene.

10.26434/chemrxiv-2024-j68gq

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New methodology to controlling regioselectivity utilizing a copper-catalyzed boracarboxylation

Mason D Hamilton Trina Perrone Brian Popp

10.1021/scimeetings.0c00823

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