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Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts.
J Am Chem Soc. 2014 Sep 24; 136(38):13198-201.JA

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.

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Authors+Show Affiliations

Hori M
Graduate School of Engineering, Nagoya University , Furo-cho, Chikusa, Nagoya 464-8603, Japan.
Sakakura A
No affiliation info available
Ishihara K
No affiliation info available

MeSH

AlanineAzo CompoundsCatalysisCationsCopperCycloaddition ReactionIminesPyrazolesStereoisomerismThiosemicarbazones

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25197958

Citation

Hori, Masahiro, et al. "Enantioselective 1,3-dipolar Cycloaddition of Azomethine Imines With Propioloylpyrazoles Induced By Chiral Π-cation Catalysts." Journal of the American Chemical Society, vol. 136, no. 38, 2014, pp. 13198-201.
Hori M, Sakakura A, Ishihara K. Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts. J Am Chem Soc. 2014;136(38):13198-201.
Hori, M., Sakakura, A., & Ishihara, K. (2014). Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts. Journal of the American Chemical Society, 136(38), 13198-201. https://doi.org/10.1021/ja508441t
Hori M, Sakakura A, Ishihara K. Enantioselective 1,3-dipolar Cycloaddition of Azomethine Imines With Propioloylpyrazoles Induced By Chiral Π-cation Catalysts. J Am Chem Soc. 2014 Sep 24;136(38):13198-201. PubMed PMID: 25197958.
* Article titles in AMA citation format should be in sentence-case
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, Y1 - 2014/09/16/ PY - 2014/9/9/entrez PY - 2014/9/10/pubmed PY - 2015/10/17/medline SP - 13198 EP - 201 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 136 IS - 38 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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/25197958/Enantioselective_13_dipolar_cycloaddition_of_azomethine_imines_with_propioloylpyrazoles_induced_by_chiral_π_cation_catalysts_ DB - PRIME DP - Unbound Medicine ER -