Synthesis and structure of macrocyclic bis(hydroxynaphthoic amide)s connected by an achiral or chiral diamine

Hiroaki Yoshida, Kazuhisa Hiratani, Tamako Ogihara, Yuka Kobayashi, Kazushi Kinbara, Kazuhiko Saigo

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Macrocyclic bis(hydroxynaphthoic amide)s 6, connected by an achiral or chiral diamine, were synthesized by the tandem Claisen rearrangement. CD spectra, X-ray crystallographic analyses, and variable-temperature NMR measurements of the chiral bis(hydroxynaphthoic amide)s revealed that the two hydroxynaphthalene rings in these macrocycles adopt a twisted conformation both in solution and in the crystalline state because of the steric hindrance between the two hydroxynaphthalene rings and that the chirality of the twisted conformation is generated by that of the chiral linker. Theoretical calculations revealed that the chiral linker works effectively to favor energetically one conformer of the diastereomers, although a flipping process was possible and can be observed to occur on the NMR time scale in variable-temperature experiments.

Original languageEnglish
Pages (from-to)5812-5818
Number of pages7
JournalJournal of Organic Chemistry
Volume68
Issue number15
DOIs
Publication statusPublished - 2003 Jul 25

ASJC Scopus subject areas

  • Organic Chemistry

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