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 |
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Pages (from-to) | 1687-1706 |
Number of pages | 20 |
Journal | Tetrahedron |
Volume | 55 |
Issue number | 6 |
DOIs | |
Publication status | Published - Feb 5 1999 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry