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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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
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Language:English
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condensation reactions
cross reaction
methodology
organic chemistry
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container_issue 24
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container_title Journal of organic chemistry
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creator Liu, Saiya
Zhang, Chenchen
Xiong, Qihua
Liu, Yuexin
Li, Lu
Sun, Yongqiang
Cheng, Bichu
Chen, Fener
description 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.
doi_str_mv 10.1021/acs.joc.3c01027
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects condensation reactions
cross reaction
methodology
organic chemistry
title Syntheses of Substituted α,β-Unsaturated δ‑Lactams from N‑Boc-2,4-dioxopiperidine
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