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 | |
| Publication status | Published - Jan 1 2019 |
Fingerprint
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 journal › Article
}
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
PY - 2019/1/1
Y1 - 2019/1/1
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.
UR - http://www.scopus.com/inward/record.url?scp=85069685762&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85069685762&partnerID=8YFLogxK
U2 - 10.3987/COM-18-S(F)92
DO - 10.3987/COM-18-S(F)92
M3 - Article
AN - SCOPUS:85069685762
VL - 99
SP - 856
EP - 864
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 2
ER -