Zinc-Catalyzed Alkyne–Carbonyl Metathesis of Ynamides with Isatins: Stereoselective Access to Fully Substituted Alkenes

A zinc-catalyzed intermolecular alkyne–carbonyl metathesis reaction of ynamides with isatins followed by an amide to ester conversion has been developed, which produces the indolone derivatives with a fully substituted alkene species in good to high yields. The salient features of this reaction incl...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-12, Vol.84 (23), p.15331-15342
Main Authors: Ao, Chaoqun, Yang, Xiaohan, Jia, Shikun, Xu, Xinfang, Yuan, Yanqiu, Zhang, Dan, Hu, Wenhao
Format: Article
Language:English
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Summary:A zinc-catalyzed intermolecular alkyne–carbonyl metathesis reaction of ynamides with isatins followed by an amide to ester conversion has been developed, which produces the indolone derivatives with a fully substituted alkene species in good to high yields. The salient features of this reaction include the following: mild reaction conditions, an inexpensive zinc catalyst, a broad substrate scope, the excellent regiocontrol and stereoselectivity, and amenable to the gram scale.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02350