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 |
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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 |
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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
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 journal › Article
}
TY - JOUR
T1 - Chiral phenylazomethine cage
AU - Shomura, Ryo
AU - Higashibayashi, Shuhei
AU - Sakurai, Hidehiro
AU - Matsushita, Yoshitaka
AU - Sato, Akira
AU - Higuchi, Masayoshi
PY - 2012/2/15
Y1 - 2012/2/15
N2 - 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.
AB - 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.
KW - C Symmetric
KW - Cavity volume
KW - Chiral phenylazomethine cage
KW - E/Z Conformation
KW - syn-Tris(norborneno)benzene
UR - http://www.scopus.com/inward/record.url?scp=84855848122&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84855848122&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2011.11.141
DO - 10.1016/j.tetlet.2011.11.141
M3 - Article
AN - SCOPUS:84855848122
VL - 53
SP - 783
EP - 785
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 7
ER -