Syntheses of Substituted α,β-Unsaturated δ‑Lactams from N‑Boc-2,4-dioxopiperidine

A method for the syntheses of substituted α,β-unsaturated δ-lactams (2) from the commercially available compound N-Boc-2,4-dioxopiperidine (1) has been developed. The α-substituents were introduced by a reductive Knoevenagel condensation reaction, and the β-substituents were installed by palladium-c...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-12, Vol.88 (24), p.17489-17493
Main Authors: Liu, Saiya, Zhang, Chenchen, Xiong, Qihua, Liu, Yuexin, Li, Lu, Sun, Yongqiang, Cheng, Bichu, Chen, Fener
Format: Article
Language:English
Subjects:
condensation reactions
cross reaction
methodology
organic chemistry
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Summary:A method for the syntheses of substituted α,β-unsaturated δ-lactams (2) from the commercially available compound N-Boc-2,4-dioxopiperidine (1) has been developed. The α-substituents were introduced by a reductive Knoevenagel condensation reaction, and the β-substituents were installed by palladium-catalyzed cross coupling reactions. More than 20 diverse examples were prepared in 2–3 steps. The synthesis was operationally simple, user-friendly, and easy to scale up.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01027