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

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	856-864
Number of pages	9
Journal	Heterocycles
Volume	99
Issue number	2
DOIs	https://doi.org/10.3987/COM-18-S(F)92
Publication status	Published - 2019

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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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, 2019, p. 856-864.

Research output: Contribution to journal › Article › peer-review

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

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",

note = "Funding Information: This research was supported by JSPS KAKENHI Grants JP16H04113 and JP18H04419 in Middle Molecular Strategy, and the Cooperative Research Program {"}NJRC Mater. & Dev.{"}. We thank T. Nishi (Kyushu University) for assistance with the HRMS measurements.",

year = "2019",

doi = "10.3987/COM-18-S(F)92",

language = "English",

volume = "99",

pages = "856--864",

journal = "Heterocycles",

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TY - JOUR

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

N1 - Funding Information: This research was supported by JSPS KAKENHI Grants JP16H04113 and JP18H04419 in Middle Molecular Strategy, and the Cooperative Research Program "NJRC Mater. & Dev.". We thank T. Nishi (Kyushu University) for assistance with the HRMS measurements.

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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