Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams

Sho ichi Iwamatsu, Hideo Kondo, Kouki Matsubara, Hideo Nagashima

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Treatment of α,α,γ-trichlorinated γ-lactams with a catalytic amount of CuCl(bipyridine) complex resulted in facile activation of their carbon- chlorine bond at the α-position. Addition of the carbon moiety and the chlorine atom to olefins furnished the carbon-carbon bond forming reaction at the α-position of the carbonyl group. In certain trichlorinated γ-lactams including a carbon-carbon double bond at an appropriate position, intramolecular addition reactions took place to give bicyclic lactams. Sequential reactions consisting of the cyclization of N-allyl trichloroacetamides followed by the inter- or intramolecular carbon-carbon bond forming reactions at the α-position of the lactams were also achieved. Efficiency of the catalyst and reaction rate was dependent on the protecting group of the nitrogen atom of the γ-lactams; N-tosyl derivatives gave better results than the corresponding N-benzyl homologues. The molecular structure of the representative products revealed the stereochemical outcome of the reactions.

Original languageEnglish
Pages (from-to)1687-1706
Number of pages20
JournalTetrahedron
Volume55
Issue number6
DOIs
Publication statusPublished - Feb 5 1999

Fingerprint

Lactams
Copper
Carbon
Chlorine
Atoms
Addition reactions
Cyclization
Alkenes
Molecular Structure
Molecular structure
Reaction rates
Nitrogen
Chemical activation
Derivatives
Catalysts

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams. / Iwamatsu, Sho ichi; Kondo, Hideo; Matsubara, Kouki; Nagashima, Hideo.

In: Tetrahedron, Vol. 55, No. 6, 05.02.1999, p. 1687-1706.

Research output: Contribution to journalArticle

Iwamatsu, Sho ichi ; Kondo, Hideo ; Matsubara, Kouki ; Nagashima, Hideo. / Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams. In: Tetrahedron. 1999 ; Vol. 55, No. 6. pp. 1687-1706.
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AB - Treatment of α,α,γ-trichlorinated γ-lactams with a catalytic amount of CuCl(bipyridine) complex resulted in facile activation of their carbon- chlorine bond at the α-position. Addition of the carbon moiety and the chlorine atom to olefins furnished the carbon-carbon bond forming reaction at the α-position of the carbonyl group. In certain trichlorinated γ-lactams including a carbon-carbon double bond at an appropriate position, intramolecular addition reactions took place to give bicyclic lactams. Sequential reactions consisting of the cyclization of N-allyl trichloroacetamides followed by the inter- or intramolecular carbon-carbon bond forming reactions at the α-position of the lactams were also achieved. Efficiency of the catalyst and reaction rate was dependent on the protecting group of the nitrogen atom of the γ-lactams; N-tosyl derivatives gave better results than the corresponding N-benzyl homologues. The molecular structure of the representative products revealed the stereochemical outcome of the reactions.

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