Synthesis and stereochemical analysis of dynamic planar chiral nine-membered diallylic amide: Significant substituent effect on stereochemical stability

Jun Ichi Hayashi, Kazuhiro Uehara, Yusuke Ano, Yuuya Kawasaki, Kazunobu Igawa, Katsuhiko Tomooka

Research output: Contribution to journalArticle

Abstract

C4-Methyl substituted nine-membered diallylic cyclic amide 1ac was synthesized. HPLC analysis using a chiral stationary phase revealed the presence of isolable enantiomers, whose absolute stereochemistry were determined by X-ray analysis. Studies on the stereochemical stability of 1ac showed that its chirality is more labile than that of the non-substituted congener 1aa and C3-methyl substituted congener 1ab.

Original languageEnglish
Pages (from-to)856-864
Number of pages9
JournalHeterocycles
Volume99
Issue number2
DOIs
Publication statusPublished - Jan 1 2019

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Stereochemistry
Enantiomers
Chirality
X ray analysis
Amides
High Pressure Liquid Chromatography
X-Rays

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Synthesis and stereochemical analysis of dynamic planar chiral nine-membered diallylic amide : Significant substituent effect on stereochemical stability. / Hayashi, Jun Ichi; Uehara, Kazuhiro; Ano, Yusuke; Kawasaki, Yuuya; Igawa, Kazunobu; Tomooka, Katsuhiko.

In: Heterocycles, Vol. 99, No. 2, 01.01.2019, p. 856-864.

Research output: Contribution to journalArticle

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