Synthesis of 1,1'-binaphthyl-2,2'-diamine from 2-naphthol under atmospheric pressure

A practical protocol to obtain 1,1′-binaphthyl-2,2′-diamine was developed from 2-naphthol and 2-naphthylhydrazine under mild conditions： solvent-free, 125-130 ℃, atmospheric pressure. The convenient procedure makes the process amenable for large-scale synthesis of the versatile compound.

A Convenient Preparation of Enantiopure 1,1'-bi-2-naphthols via an Inclusion Complexation in the Solid State

Inclusion reaction of reaction 1, 1'-bi-2-naphthol and (S)-proline was examined uuder the solid state and the solid-liquid conditions. The results indicated that a solid mixture of racemic 1, 1'-bi-2-naphthol and (S)-proline in a 1 : 1 molar ratio was kept at 50-80 for 3-4 h, followed by treatment with benzene to give an insoluble solid and a benzene solution, from which (S)- (- )- and (R)-(+)-1, 1'-bi-2-naphthols of a modest level or optical purity were obtained. Arter 'kinetic' crystallization, both essentially enantiopure iso- mers were provided in 15%-35 % overall yields ,respectively.

Design and synthesis of chiral Ti-1,1′-bi-2-naphthol coordination polymers for heterogeneous catalytic asymmetric oxidation of sulfides

Polymer-immobilized catalysis has many advantages such as easy recovery and reuse of catalyst. We prepared three novel chiral 1,1＇-bi-2-naphthol-Ti coordination polymers with properly designed ligands and Ti（O^ipr）4 under mild conditions. The prepared polymers exhibited good activity and excellent enantioselectivity （over 99%ee） in catalyzing the asymmetric oxidation of sulfides. The bridge linker in the polymer and the reaction solvent noticeably affected the enantioseleetivity. The chiral coordination polymer was very stable and easy to separate from catalyzed reaction systems, with no significant loss of activity or enantioselectivity after reuse for at least ten times. These findings suggest a promising type of catalysts for synthesizing the widely used sulfoxides by asymmetrically oxidizing sulfides.

Synthesis of Hymecromone Derivatives Containing Chiral 1,1'-Bi-2-naphthyl Moiety for Dual-mode Molecular Switch

Some hymecromone derivatives containing chiral 1,1'-bi-2-naphthyl moiety were synthesized and their photodimerizations were investigated. It was found that fluorescence intensity and optical rotation of the new chiral hymecromone derivatives could be regulated by light. This property has potential significance for developing a new type of dual-mode molecular switch.

Immobilizing BINOL via Suzuki Reaction:Synthesis and Application in Catalytic Asymmetric Oxidation of Sulfide to Sulfoxide

Immobilizing chiral 1,1＇-bi-2-naphthol （BINOL） in one step onto polymer backbone via stable carbon-carbon bond through Suzuki reaction was achieved. The application of this immobilized chiral BINOL to the catalytic asymmetric oxidation of sulfide to sulfoxide exhibited good activity （up to 60% yield） and high enantioselectivity （up to 89% ee）. The immobilized chiral catalyst was very stable and could be readily reused for over 5 times without significant loss of catalytic activity and enantioselectivity.

A Facile Synthesis of Enantiomerically Pure （R）-6-Arylbinols

This work reported a convenient method for the preparation of enantiomerically pure 6-aryl-2,2＇-dihydroxy-1, l＇- binaphthyl derivatives starting from the commercially available （R）-2,2＇-hydroxy-l, l＇-binaphthyl [（R）-I] via bromi- nation, hydrolysis and Suzuki cross coupling reaction. This novel synthetie method was characterized with high re- gioselectivity, simple operation, mild reaction conditions, and excellent yield （up to 73%）. On the other hand, we synthesized the target unknown compounds, which were confirmed by IR, 1H NMR, 13C NMR, MS and elementary analysis.