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

doi:10.1016/S0040-4020(98)01198-3

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

Applied Molecular Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1687-1706
Number of pages	20
Journal	Tetrahedron
Volume	55
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4020(98)01198-3
Publication status	Published - 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

Iwamatsu, S. I., Kondo, H., Matsubara, K., & Nagashima, H. (1999). Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams. Tetrahedron, 55(6), 1687-1706. https://doi.org/10.1016/S0040-4020(98)01198-3

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 journal › Article

Iwamatsu, SI, Kondo, H, Matsubara, K & Nagashima, H 1999, 'Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams', Tetrahedron, vol. 55, no. 6, pp. 1687-1706. https://doi.org/10.1016/S0040-4020(98)01198-3

Iwamatsu SI, Kondo H, Matsubara K, Nagashima H. Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams. Tetrahedron. 1999 Feb 5;55(6):1687-1706. https://doi.org/10.1016/S0040-4020(98)01198-3

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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10.1016/S0040-4020(98)01198-3