Synthesis of dienes from pyrrolidines using skeletal modification Article Swipe

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Haitao Qin , Ting Guo , Ken Lin , Guigen Li , Hongjian Lu ·

YOU? · · 2023 · Open Access · · DOI: https://doi.org/10.1038/s41467-023-43238-7

Saturated N-heterocyclic pyrrolidines are common in natural products, medicinal compounds and agrochemicals. However, reconstruction of their skeletal structures creating new chemical space is a challenging task, and limited methods exist for this purpose. In this study, we report a skeletal modification strategy for conversion of polar cyclic pyrrolidines into nonpolar linear dienes through a N-atom removal and deconstruction process. This involves N-sulfonylazidonation followed by rearrangement of the resulting sulfamoyl azide intermediates. This can be an energetically unfavorable process, which involves the formation of active C–C π bonds, the consumption of inert C–N and C–C σ bonds and the destruction of stable five-membered rings, but we have used it here to produce versatile conjugated and nonconjugated dienes with links of varying lengths. We also studied the application of this method in late-stage skeletal modification of bioactive compounds, formal traceless C(sp 2 )–H functionalization and formal N-atom deletion.

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Type: article
Language: en
Landing Page: https://doi.org/10.1038/s41467-023-43238-7
PDF: https://www.nature.com/articles/s41467-023-43238-7.pdf
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Cited By: 16
References: 53
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DOI: https://doi.org/10.1038/s41467-023-43238-7

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Title: Synthesis of dienes from pyrrolidines using skeletal modification

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Language: en

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Publication year: 2023

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Publication date: 2023-11-11

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Authors: Haitao Qin, Ting Guo, Ken Lin, Guigen Li, Hongjian Lu

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Landing page: https://doi.org/10.1038/s41467-023-43238-7

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Concepts: Chemistry, Combinatorial chemistry

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Cited by: 16

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