Chiral phenylazomethine cage

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

Research output: Contribution to journalArticle

7 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
Externally publishedYes

Fingerprint

Chirality
Benzene
Dehydration
Discrete Fourier transforms
X-Ray Diffraction
Nuclear magnetic resonance
X ray diffraction
4-phenylenediamine
phenylazomethine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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

Chiral phenylazomethine cage. / Shomura, Ryo; Higashibayashi, Shuhei; Sakurai, Hidehiro; Matsushita, Yoshitaka; Sato, Akira; Higuchi, Masayoshi.

In: Tetrahedron Letters, Vol. 53, No. 7, 15.02.2012, p. 783-785.

Research output: Contribution to journalArticle

Shomura, R, Higashibayashi, S, Sakurai, H, Matsushita, Y, Sato, A & Higuchi, M 2012, 'Chiral phenylazomethine cage', Tetrahedron Letters, vol. 53, no. 7, pp. 783-785. https://doi.org/10.1016/j.tetlet.2011.11.141
Shomura R, Higashibayashi S, Sakurai H, Matsushita Y, Sato A, Higuchi M. Chiral phenylazomethine cage. Tetrahedron Letters. 2012 Feb 15;53(7):783-785. https://doi.org/10.1016/j.tetlet.2011.11.141
Shomura, Ryo ; Higashibayashi, Shuhei ; Sakurai, Hidehiro ; Matsushita, Yoshitaka ; Sato, Akira ; Higuchi, Masayoshi. / Chiral phenylazomethine cage. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 7. pp. 783-785.
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