Macrocyclic amides consisting of helical chiral 1,12- dimethylbenzo[c]phenanthrene-5,8-dicarboxylate

Hitoshi Okubo, Masahiko Yamaguchi, Chizuko Kabuto

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60 Citations (Scopus)

Abstract

Helical chiral 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid was synthesized and resolved in multigram quantities. The absolute configuration was determined by X-ray analysis of the bis(camphorsultamamide) derivative. A series of optically active macrocyclic amides consisting of the chiral unit and a dianiline spacer were synthesized by one-pot procedures, and their structures were compared by spectroscopy and X-ray crystallography. One of the cycloamides exhibited catalytic activity in the asymmetric addition of diethylzinc to aromatic aldehydes. N-Alkylated derivatives were also synthesized, which possessed folded structures distinct from those of the parent cyclic amides.

Original languageEnglish
Pages (from-to)9500-9509
Number of pages10
JournalJournal of Organic Chemistry
Volume63
Issue number25
DOIs
Publication statusPublished - 1998 Dec 11

ASJC Scopus subject areas

  • Organic Chemistry

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