Shiyuan Sui,Hao Wu,Yuanyuan Guo,Gongming Chen,Junbiao Chang,Dachang Bai
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Enantioselective Synthesis of ε-Lactams via Rh(I)-Catalyzed C─C Bond Activation.
ε-Lactams are important structural motifs in medicinal chemistry, but a fully enantioselective synthesis without byproduct formation represents a challenge that has attracted significant research interest. Herein, we report an atom- and step-economic synthesis of chiral ε-lactams via Rh(I)-catalyzed enantioselective C─C bond activation of aminocyclopropanes. The catalytic C─C bond activation enables a directed generation of chiral rhodacyclobutanes that circumvents β-hydride decomposition. Subsequent enantioselective cycloaddition of the alkene unit and then fragmentation generates chiral ε-lactams. A range of enantioenriched ε-lactams have been obtained with excellent regio- and enantioselectivities, which can undergo several stereospecific transformations. Theoretical calculations are performed to reveal the reaction mechanism and the origin of enantioselectivity control.
期刊介绍:
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.