Here we present a simple, one-step synthesis of (R)-(+)-2'-Amino-1,1'-binaphthalen-2-ol (NOBIN) using (R)-(+)-1,1'-Binaphthyl-2,2'-diamine (BINAM) as a starting material under acidic aqueous conditions in the presence of peroxides. Axially chiral, enantiomerically pure NOBIN and its derivatives are a popular class of ligands used in a wide range of asymmetric catalytic reactions, including several on an industrial scale. Such biaryl motifs are also important pharmacophores in natural products and have implications in the development of pharmaceuticals. Multiple solvents, peroxides, temperatures, and acid concentrations were evaluated to determine the optimal reaction conditions. Yields in excess of 70% were obtained by dissolving 5mg/mL R-BINAM with equivalent moles of peroxide in mixture of 1,4-Dioxane and 20% HCl and heated at 85 �C for several hours. Preparative HPLC was used to purify the final product. Reactions were monitored by chiral HPLC and the products were characterized by High-Resolution Mass Spectrometry and NMR. BINAM and NOBIN stereochemistry was maintained throughout the reaction and no racemization of product was observed. The novel one-step reaction is the first of its kind to provide enantiomerically pure NOBIN without any use of toxic metal catalysts and provides high yields. Investigations into the plausible reaction mechanism will be discussed.

Facile approach to convert (R)-BINAM to (R)-NOBIN using peroxide under acidic conditions

247th National Meeting (2014)

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