Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton

Masaya Suzuki, Yoshihiro Nishida, Yuya Ohguro, Yoshiko Miura, Akiko Tsuchida, Kazukiyo Kobayashi

研究成果: Contribution to journalArticle査読

7 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)159-165
ページ数7
ジャーナルTetrahedron Asymmetry
15
1
DOI
出版ステータス出版済み - 1 12 2004
外部発表はい

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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