Preparation of Enantiomerically Pure 1,1'-Bi-2-naphthols from 85% Cinchonine and 1,1'-Bi-2-naphtholboric Anhydride

A possibility of preparation of enantiomerically pure 1,1' bi 2 naphthols using an impure cinchonine has been examined. The solid and the mother liquor formed from the reaction of 1,1' bi 2 naphtholboric anhydride and 85 % cinchonine in toluene could give optically pure (S) ( ) and (R) (+) 1,1' bi 2 naphthol after acidification and kinetic crystallization, the overall yields were 40 % and 28 %, respectively.

Selective recognition in molecularly imprinted polymer and its chromatographic characterization for cinchonine

A molecularly imprinting polymer (MIP) was synthesized via bulk polymerization under different conditions using anti-ague drug cinchonine (CN) as template. Infrared spectra (IR) results show that the template CNand functional monomer α-methyl acrylic acid (MAA) formed complexes before polymerization and the structure of complexes was simulated by Hyperchem. The results indicate that there are hydrogen bond or ionic bond between functional monomer and template molecule in acetonitrile solution. The MIP made in cold-initiated photo-polymerization has higher separation performance than that in the therm-initiated polymerization. The separation of the isomers CN and cinchonidine (CD) can be successfully obtained when its separate factor α reaches 1.82. Scatchard analysis suggests that the MIP recognizing CN with two classes of binding sites. The partition coefficient Kd, 1 and apparent maximum number nmax, 1 of binding sites with high affinity are 131.43 μmol/L and 58. 90 μmol/g, respectively,while Kd, 2 and nmax, 2 of binding sites with low affinity are 2.32 mmol/L and 169.08 mmol/g, respectively.

Catalytic Enantioselective Methanolysis of 4 -substituted-2-phenyl-5(4H)-oxazolones by Cinchonine

Cinchonine alkaloid catalyzed enantioselective methanolysis of six 4-substituted 2-phenyl-5(4H)-oxazolones to (S)-methyl N-benzoyl-alpha-amino acid esters with 10-33% e.e and 72-81% yield.

The First Homochiral Diamond-Like Coordination Polymer Containing Cubane Cluster （Cu4I4） as Connecting Node and Cinchonine as Donor-Acceptor （or Push-Pull Electronic Effect） Building Block

The reaction of CuI with cinchonine （an organic donor-acceptor chromophore） afforded a homochiral 3D diamondoid network [Cu4I4（cinchonine）2]n （1） containing a cubane cluster （Cu4I4） as a connecting node. This is the first homochiral coordination polymer with diamondoid nets containing a cluster as a connecting note. Its thermal stability and solid state optical properties such as fluorescence, circular dichroism and second-harmonic generation response were also reported.

Enantioselective Addition of Phenylacetylene to Ketones Catalyzed by Chiral Amino Alcohols

（S）-（1-Benzylpyrrolidin-2-yl）diphenylmethanol and cinchonine were evaluated as promotors in the asymmetric additions of phenylacetylene to ketones, in order to prepare chiral propargylic alcohols. Good yields （up to 89%） and moderate enantioselectivities （up to 77.9% ee） were achieved. Addition of Ti（OPr-i）4 can significantly improve the enantioselectivity of the reaction.