Binaphthol, chiral discrimination

The chiral discrimination process studied for quinine and binaphthol 29 (R = i-Pr) by using 1H NMR spectroscopy led to the conclusion that the primary forces responsible for the enantiodiscrimination are the hydrogen bonds and steric interactions [57, 58], Optimization studies on quinine for the enantioseparation of carbinol 28 (Ar = 9-anthryl, R = CF3) on quinine CSP 25 carried out by Nesterenko et al. showed that under normal conditions the best selectivity (a 1.53) could be... 

Liu T, Chen Y, Zhang K et al (2001) Enantiomeric recognition of chiral 3,3-bridged-l,r-binaphthol dimer toward a-phenylethylamine and a-amino acid ester. Chirality 13 595-600 Beer G, Daub J, Rurack K (2001) Chiral discrimination with a fluorescent boron-dipyrromethene dye. Chem Commun 1138-1139... 

Enantiotopos discrimination, 93, 128, 142, 234, 235, 331 Ene reactions asymmetric, 223 binaphthol, 222 chiral metal complexes, 222 intramolecular, 226 methyl glyoxylate, 290 Enol silyl ether substrates, 128, 228, 230 Enol substrates, 28 Enolates ... 

Yamamoto and Maruoka have reported the first aluminum-promoted asymmetric Claisen rearrangement [5]. They used a chiral 3,3 -bis(triarylsilyl)-substi-tuted binaphthol (BINOL) aluminum reagent 1 to promote the enantioselective coordination to one of the two enantiomeric oxygen lone pairs of 2. Enantioselective discrimination is based on two chair-hke transition states A and B to give two enantiomeric products 3, respectively (Scheme 2.2). 

Zhang XH, Wang Y, Jin WJ (2008) Enantiomeric discrimination of l,l -binaphthol by room temperature phosphorimetry using y-cyclodextrin as chiral selector. Anal Chim Acta 622 157-162... 

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