TY - JOUR
T1 - Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton
AU - Suzuki, Masaya
AU - Nishida, Yoshihiro
AU - Ohguro, Yuya
AU - Miura, Yoshiko
AU - Tsuchida, Akiko
AU - Kobayashi, Kazukiyo
N1 - Funding Information:
A part of this study was supported in part by a grant from the 21st Century COE program ‘Nature-Guided Materials Processing’ of the Ministry of Education, Culture, Sport, Science and Technology of Japanese Government.
PY - 2004/1/12
Y1 - 2004/1/12
N2 - 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, 1H 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.
AB - 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, 1H 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.
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U2 - 10.1016/j.tetasy.2003.10.030
DO - 10.1016/j.tetasy.2003.10.030
M3 - Article
AN - SCOPUS:0346787835
SN - 0957-4166
VL - 15
SP - 159
EP - 165
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 1
ER -