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Letters in Organic Chemistry

Author(s): İrfan Çapan and Süleyman Servi*

DOI: 10.2174/1570178616666190731105327

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Synthesis of New C2-Symmetric Chiral Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons

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Abstract

Racemic dicarboxylic acids were synthesized from the Diels-Alder cycloaddition reactions which formed the dibenzobarrelene and norbornene skeletons. The pure enantiomers of these compounds were obtained using brucine as the chiral auxiliary. Novel C2-symmetric chiral benzimidazole derivatives were synthesized from the reaction of the diaminobenzene and enantiomeric dicarboxylic acids in the presence of boric acid.

Keywords: Norbornene, dibenzobarrelene, guanidine, benzimidazole, chiral resolution.

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