Chiral phenylazomethine cage

Ryo Shomura, Shuhei Higashibayashi, Hidehiro Sakurai, Yoshitaka Matsushita, Akira Sato, Masayoshi Higuchi

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 languageEnglish
Pages (from-to)783-785
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number7
DOIs
Publication statusPublished - 2012 Feb 15

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Keywords

  • C Symmetric
  • Cavity volume
  • Chiral phenylazomethine cage
  • E/Z Conformation
  • syn-Tris(norborneno)benzene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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