Radical Chain Isomerization of N‑Sulfonyl Ynamides to Ketenimines and Its Application to Furan Dearomatization

Radical Chain Isomerization of N‑Sulfonyl Ynamides to Ketenimines and Its Application to Furan Dearomatization

A radical chain isomerization of N-sulfonyl ynamides to isolable ketenimines is developed, featuring mild reaction conditions, a high efficiency, ∼100% atom economy, a broad substrate scope, and column chromatography-free workup in most cases. Meanwhile, an unprecedented dearomatization of furans is...

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Veröffentlicht in:Organic letters 2021-12, Vol.23 (23), p.9321-9326
Hauptverfasser: Shen, Jiahuan, Wu, Zhenzhen, Liu, Yi, Bai, Yihui, Qiu, Jiayan, Zhang, Zuxiao, Yuan, Zheliang, Zhu, Gangguo
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container_end_page 9326
container_issue 23
container_start_page 9321
container_title Organic letters
container_volume 23
creator Shen, Jiahuan
Wu, Zhenzhen
Liu, Yi
Bai, Yihui
Qiu, Jiayan
Zhang, Zuxiao
Yuan, Zheliang
Zhu, Gangguo
description A radical chain isomerization of N-sulfonyl ynamides to isolable ketenimines is developed, featuring mild reaction conditions, a high efficiency, ∼100% atom economy, a broad substrate scope, and column chromatography-free workup in most cases. Meanwhile, an unprecedented dearomatization of furans is achieved by the radical chain isomerization-triggered aza-Claisen rearrangement, providing highly chemo-, regio-, stereo-, and diastereoselective access to functionalized quaternary nitriles.
doi_str_mv 10.1021/acs.orglett.1c03729
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title Radical Chain Isomerization of N‑Sulfonyl Ynamides to Ketenimines and Its Application to Furan Dearomatization
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