“Cut-and-Sew” Reactions of β-Lactams via C–C Bond Activation

Transition metal-catalyzed "cut-and-sew" reactions offer an efficient approach to construct bridged and fused scaffolds; however, the substrates have been primarily restricted to cyclic ketones and activated cyclopropanes. Here we report the first cut-and-sew transformation between β-lactams and alkenes/alkynes via C-C bond activation. Diverse bridged and fused nitrogen-heterocycles are prepared using this method with good functional group tolerance. The synthetic utility is demonstrated in the unified and streamlined preparation of norbenzomorphan-containing bioactive compounds.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-09-08
DOI
https://doi.org/10.1021/jacs.5c12770
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

“Cut-and-Sew” Reactions of β-Lactams via C–C Bond Activation

Liyan Kan, Yoshiyuki Hari, Guangbin Dong, Rui Zhang et al.
Journal of the American Chemical Society
Cyclopropane Reaction Mechanisms
article

“Cut-and-Sew” Reactions of β-Lactams via C–C Bond Activation

Liyan Kan, Yoshiyuki Hari, Guangbin Dong, Rui Zhang, Shou-Lin Lu
article en

Abstract

Transition metal-catalyzed "cut-and-sew" reactions offer an efficient approach to construct bridged and fused scaffolds; however, the substrates have been primarily restricted to cyclic ketones and activated cyclopropanes. Here we report the first cut-and-sew transformation between β-lactams and alkenes/alkynes via C-C bond activation. Diverse bridged and fused nitrogen-heterocycles are prepared using this method with good functional group tolerance. The synthetic utility is demonstrated in the unified and streamlined preparation of norbenzomorphan-containing bioactive compounds.

Journal of the American Chemical SocietyVol. 147(37)
University of Chicago (US)
Openalex Percentile: Top 82%
Cyclopropane Reaction Mechanisms
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