Abstract
Enantiopure phenylazomethine cages ((S)- and (R)-PAC) were selectively obtained by one-pot dehydration of chiral (S)- and (R)-syn-tris(norborneno) benzene with p-phenylenediamine in moderate yields (56% and 50%), respectively. The structure and chirality of PACs in solution and solid state were confirmed by NMR, CD, X-ray diffraction and DFT calculations.
| Original language | English |
|---|---|
| Pages (from-to) | 783-785 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 53 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 2012 Feb 15 |
| Externally published | Yes |
Keywords
- C Symmetric
- Cavity volume
- Chiral phenylazomethine cage
- E/Z Conformation
- syn-Tris(norborneno)benzene
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Shomura, R., Higashibayashi, S., Sakurai, H., Matsushita, Y., Sato, A., & Higuchi, M. (2012). Chiral phenylazomethine cage. Tetrahedron Letters, 53(7), 783-785. https://doi.org/10.1016/j.tetlet.2011.11.141