(R)-(6,6′-Dihydroxybiphenyl-2,2′-diyl)bis(diphenylphosphine oxide) methanol solvate

Abstract

The title compound, C36H28O4P2·CH4O, was synthesized directly from the methoxy analogue. The crystal structure shows that one OH group interacts with an O atom of a phosphine oxide group in an adjacent mol­ecule, while the other OH group complexes with the methanol solvent molecule via intermolecular hydrogen bonds. An O atom of one phosphine oxide group interacts with the hydroxy H atom of methanol via a hydrogen bond. There are intra‐ and intermolecular π–π interactions between the phenyl rings. All these interactions result in the formation of supramolecular chiral parallelogram channels via self‐assembly.

A New Class of Versatile Chiral-Bridged Atropisomeric Diphosphine Ligands: Remarkably Efficient Ligand Syntheses and Their Applications in Highly Enantioselective Hydrogenation Reactions

“…At the outset, demethylation of ( S )- or ( R )-MeO-BiphepO 8 with BBr 3 followed by hydrolysis furnished ( S )- or ( R )-HO-BiphepO 9 in 75% and 78% yields, respectively . Subsequently, ( S )- or ( R )- 9 reacted with (2 R ,3 R )-butanediol dimesylate (2a) in the presence of Cs 2 CO 3 afforded ( SSS )- 6a or its diastereomer ( RSS )- 6a in 58% and 64% yields, respectively.…”

“…Synthesis of ( R ) - (6,6 ‘ -Dihydroxybiphenyl-2,2 ‘ -diyl)bis(diphenylphosphine oxide) (( R )-9). ( R )- 9 was prepared from ( R )- 8 by following the same procedure reported in the literature as a white powder (85.0% conversion, 91.6% selectivity) …”

Allosteric P═O-Based Receptors for Dicarboxylic Acids

“…New receptors rac - 3a – e were straightforwardly synthesized from easily available compound rac - 1 by reaction with the corresponding bistosylated polyethylene oxide derivative 2 and an excess of Cs 2 CO 3 (10 equiv) in DMF at 60 °C for 24 h. Compounds rac - 3a – e were isolated as white solids in 42–65% yield (Scheme ) and characterized by standard analytical methods (NMR and HRMS). X-ray analysis confirmed the proposed structures.…”