Abstract
We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-L-alanine amide. The asymmetric environment created by intramolecular π - cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.
| Original language | English |
|---|---|
| Pages (from-to) | 13198-13201 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 136 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - Sep 24 2014 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
- Medicine(all)
Cite this
Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts. / Hori, Masahiro; Sakakura, Akira; Ishihara, Kazuaki.
In: Journal of the American Chemical Society, Vol. 136, No. 38, 24.09.2014, p. 13198-13201.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts
AU - Hori, Masahiro
AU - Sakakura, Akira
AU - Ishihara, Kazuaki
PY - 2014/9/24
Y1 - 2014/9/24
N2 - We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-L-alanine amide. The asymmetric environment created by intramolecular π - cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.
AB - We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-L-alanine amide. The asymmetric environment created by intramolecular π - cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.
UR - http://www.scopus.com/inward/record.url?scp=84924692313&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84924692313&partnerID=8YFLogxK
U2 - 10.1021/ja508441t
DO - 10.1021/ja508441t
M3 - Article
C2 - 25197958
AN - SCOPUS:84924692313
VL - 136
SP - 13198
EP - 13201
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 38
ER -