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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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, 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.

Original languageEnglish
Pages (from-to)159-165
Number of pages7
JournalTetrahedron Asymmetry
Volume15
Issue number1
DOIs
Publication statusPublished - Jan 12 2004
Externally publishedYes

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Nitrobenzoates
Enantiomers
enantiomers
musculoskeletal system
nitration
Nitration
acids
Acids
synthesis
Nuclear magnetic resonance
nuclear magnetic resonance
Dichroism
Crystallization
Amides
linkages
carboxylates
Peptides
amides
dichroism
peptides

All Science Journal Classification (ASJC) codes

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

Cite this

Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton. / Suzuki, Masaya; Nishida, Yoshihiro; Ohguro, Yuya; Miura, Yoshiko; Tsuchida, Akiko; Kobayashi, Kazukiyo.

In: Tetrahedron Asymmetry, Vol. 15, No. 1, 12.01.2004, p. 159-165.

Research output: Contribution to journalArticle

Suzuki, Masaya ; Nishida, Yoshihiro ; Ohguro, Yuya ; Miura, Yoshiko ; Tsuchida, Akiko ; Kobayashi, Kazukiyo. / Synthesis and characterization of asymmetric o- and m-nitrobenzoic acids with a 1,3-benzodioxole skeleton. In: Tetrahedron Asymmetry. 2004 ; Vol. 15, No. 1. pp. 159-165.
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AU - Kobayashi, Kazukiyo

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