Enantioselective Synthesis of Atropisomeric Biaryl Phosphorus Compounds by Chiral-Phosphonium-Salt-Enabled Cascade Arene Formation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2022)

Cited 14|Views12
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Abstract
Axially chiral biaryl monophosphorus molecules, exemplified by atropisomeric 1,1 '-biaryl aminophosphines, are significant motifs in numerous chiral ligands/catalysts. Developing efficient methods for preparing phosphorus compounds with these privileged motifs is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a chiral-phosphonium-salt-catalyzed novel cascade between phosphorus-containing nitroolefins and alpha,alpha-dicyanoolefins, leading to a great diversity of atropisomeric biaryls bearing phosphorus groups in high yields with excellent stereoselectivities. The reaction features include a Thorpe-type cycloaddition/oxidative hydroxylation/aromatization cascade pathway with a central-to-axial chirality transfer process. Insight gained from our studies is expected to advance general efforts towards the catalytic synthesis of atropisomeric biaryl phosphorus compounds, offering a platform for developing new efficient chiral ligands and catalysts.
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Key words
Atropisomerism, Biaryl Phosphines, Central-to-Axial Chirality Transfer, Enantioselective Cascade Reactions, Phosphonium Salts
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