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

doi:10.3987/COM-18-S(F)92

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

分子集積化学部門

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

2 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	856-864
ページ数	9
ジャーナル	Heterocycles
巻	99
号	2
DOI	https://doi.org/10.3987/COM-18-S(F)92
出版ステータス	出版済み - 2019

!!!All Science Journal Classification (ASJC) codes

分析化学
薬理学
有機化学

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10.3987/COM-18-S(F)92

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引用スタイル

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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.",

author = "Hayashi, {Jun Ichi} and Kazuhiro Uehara and Yusuke Ano and Yuuya Kawasaki and Kazunobu Igawa and Katsuhiko Tomooka",

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T1 - Synthesis and stereochemical analysis of dynamic planar chiral nine-membered diallylic amide

T2 - Significant substituent effect on stereochemical stability

AU - Hayashi, Jun Ichi

AU - Uehara, Kazuhiro

AU - Ano, Yusuke

AU - Kawasaki, Yuuya

AU - Igawa, Kazunobu

AU - Tomooka, Katsuhiko

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

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