Phosphine-Promoted Tandem Intermolecular Diels–Alder Reactions with Pentadienyl 4‑Nitrobenzoate as a Diene Precursor

A phosphine-promoted tandem Diels–Alder reaction using pentadienyl 4-nitrobenzoate (α-vinyl MBH adduct) as a diene precursor with 3-olefinic oxindoles or CF3-activated ketones as dienophiles has been developed. The reaction proceeds through the formation of a pentadienyl phosphonium intermediate via...

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Bibliographic Details
Published in:Organic letters 2023-09, Vol.25 (35), p.6506-6510
Main Authors: Zhang, Le, Liu, Ye, Li, Chao-Xu, Zhu, Lei, Xiong, Guo-Yin, Fan, Shi-Lu, Dai, Jian-Jun, Xiao, Hua
Format: Article
Language:English
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Summary:A phosphine-promoted tandem Diels–Alder reaction using pentadienyl 4-nitrobenzoate (α-vinyl MBH adduct) as a diene precursor with 3-olefinic oxindoles or CF3-activated ketones as dienophiles has been developed. The reaction proceeds through the formation of a pentadienyl phosphonium intermediate via SN2′′ addition, which acts as both a D–A diene and a precursor for the exomethylene moiety. This method offers a metal-free and step-efficient approach for synthesizing exomethylene-bearing spirooxindoles and dihydropyrans, which are privileged structures found in natural products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02209