Catalytic enantioselective 1,3-dipolar cycloadditions of nitrones with propioloylpyrazoles and acryloylpyrazoles induced by chiral π-cation catalysts

Akira Sakakura, Masahiro Hori, Makoto Fushimi, Kazuaki Ishihara

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

A chiral copper(II) complex of 3-(2-naphthyl)-l-alanine amide successfully catalyzes the enantioselective 1,3-dipolar cycloaddition reaction of nitrones with propioloylpyrazole and acryloylpyrazole derivatives. The asymmetric environment created by intramolecular π-cation interaction 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 nitrones with acetylene derivatives. The 1,3-dipolar cycloadducts can be stereoselectively converted to β-lactams via reductive cleavage of the N-O bond using SmI2.

Original languageEnglish
Pages (from-to)15550-15552
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number44
DOIs
Publication statusPublished - Nov 10 2010
Externally publishedYes

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Cycloaddition
Cycloaddition Reaction
Cations
Positive ions
Derivatives
Lactams
Acetylene
Catalysts
Enantioselectivity
Amides
Alanine
Copper
nitrones
3-(2-naphthyl)alanine

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Catalytic enantioselective 1,3-dipolar cycloadditions of nitrones with propioloylpyrazoles and acryloylpyrazoles induced by chiral π-cation catalysts. / Sakakura, Akira; Hori, Masahiro; Fushimi, Makoto; Ishihara, Kazuaki.

In: Journal of the American Chemical Society, Vol. 132, No. 44, 10.11.2010, p. 15550-15552.

Research output: Contribution to journalArticle

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