1.Lewis acid template-catalyzed asymmetric diels-alder reaction.
Ishihara J1, Nakadachi S, Watanabe Y, Hatakeyama S. J Org Chem. 2015 Feb 20;80(4):2037-41. doi: 10.1021/acs.joc.5b00055. Epub 2015 Jan 29.
An asymmetric Diels-Alder reaction of 2,4-dienols and methyl acrylate utilizing a chiral Zn(II)/Mg(II) bimetallic template with low catalyst loading was successfully achieved. The bimetallic Lewis acid template derived from (R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol catalyzed the Diels-Alder reaction in the presence of molecular sieves 4 Å to afford various functionalized bicyclic γ-lactones with high enantiomeric purities.
2.Chiral separation of 1,1'-bi-2-naphthol and its analogue on molecular imprinting monolithic columns by HPLC.
Ou J1, Tang S, Zou H. J Sep Sci. 2005 Nov;28(17):2282-7.
Two molecular imprinting polymer (MIP) monolithic columns with (S)-(-)-1,1'-bi-2-naphthol and (R)-(+)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol as the templating molecules, respectively, have been prepared by in situ polymerization using 4-vinylpyridine and ethylene dimethacrylate as functional monomer and cross-linker, respectively. The columns with good flow-through properties were obtained by changing the molar ratio of the functional monomer and the template molecule. The effects of mobile-phase composition on separation of enantiomers were systematically investigated. The results indicate that hydrophobic interaction in aqueous solution and hydrogen-bonding interaction in ACN between the enantiomers and polymers could play important roles in the retention and resolution. The effects of chromatographic conditions, such as flow rate, column temperature, sample loading, on the enantioseparation were also studied. Further, these two MIP columns show a cross-reactivity.
