Designing P*-chirogenic Organophosphorus Compounds: from Ligands to Organocatalysts

GRAPHICAL ABSTRACT

Abstract

The interest of organophosphorus compounds bearing chirality on the phosphorus atom has greatly expanded in last decade, due to the development of efficient stereoselective synthetic methods, using menthol, ephedrine, sparteine, or α-arylethylamine as chiral auxiliaries, and phosphine borane chemistry. Today, the efficient design of P-chirogenic organophosphorus compounds can be achieved using electrophilic or nucleophilic stereoselective reactions at the P-center, to afford a large variety of derivatives with P*-C, P*-H, P*-Cl, P*-O, or P*-N bond formation. Recent progress of the ephedrine methodology was illustrated by the enantiodivergent synthesis of new classes of P-chirogenic ligands, phosphonium salts or organocatalysts, and their uses for the preparation of chiral coordinating polymers and clusters, or in asymmetric catalyzed and organocatalyzed reactions.

Keywords:

• P-chirogenic phosphines
• phosphine boranes
• o-functionalized phosphines
• phosphonium salts
• asymmetric catalysis
• coordinating polymers
• organocatalysis