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 |
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Hayashi, J. I., Uehara, K., Ano, Y., Kawasaki, Y., Igawa, K., & Tomooka, K. (2019). Synthesis and stereochemical analysis of dynamic planar chiral nine-membered diallylic amide: Significant substituent effect on stereochemical stability. Heterocycles, 99(2), 856-864. https://doi.org/10.3987/COM-18-S(F)92