Chiral phenylazomethine cage

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

doi:10.1016/j.tetlet.2011.11.141

Chiral phenylazomethine cage

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	783-785
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2011.11.141
Publication status	Published - 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

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AU - Higuchi, Masayoshi

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Access to Document

10.1016/j.tetlet.2011.11.141