Masaya Suzuki, Y. Nishida, Yuya Ohguro
Jan 12, 2004
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Asymmetric o - and m -nitrobenzoic acids with a 1,3-benzodioxole skeleton have been synthesized and characterized. The synthesis involved nitration at either the C-5 or C-6 position of 2- tert -butyl-2-methyl-1,3-benzodioxole-4-carboxylate derived from catechol. These were then resolved with chiral solid-phased HPLC columns into each of enantiomers (>99% ee), which were characterized by circular dichroism. The ( S )-enantiomers were also obtained by fractional crystallization of the precursor prior to the nitration. When applied as chiral derivation agents for alcohols and amines, m -nitrobenzoic acid showed notable ability to separate the enantiomers in both HPLC and NMR analyses. On the other hand, 1 H NMR and X-ray data of their ester and amide derivatives strongly suggested that the o -nitrobenzoic acid would serve as a fluorescent building block useful for the assembly of β-peptide linkages with a defined conformation.