Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts

Masahiro Hori, Akira Sakakura, Kazuaki Ishihara

Research output: Contribution to journalArticle

36 Citations (Scopus)

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 languageEnglish
Pages (from-to)13198-13201
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number38
DOIs
Publication statusPublished - Sep 24 2014

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Imines
Cycloaddition
Cycloaddition Reaction
Cations
Positive ions
Catalysts
Alkynes
Enantioselectivity
Amides
Alanine
Copper
Ligands
Derivatives
azomethine
3-(2-naphthyl)alanine

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 journalArticle

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