Cu(OAc)2‑Triggered Cascade Reaction of Malonate-Tethered Acyl Oximes with Indoles, Indole-2-alcohols, and Indole-2-carboxamides

A Cu­(OAc)2-promoted cascade reaction of malonate-tetherd acyl oximes with indoles, indole-2-alcohols, or indole-2-carboxmides provides facile access to polysubstituted 3-pyrrolin-2-ones. The reaction features the generation of two adjacent electrophilic centers at the same time as cyclization to la...

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Bibliographic Details
Published in:Organic letters 2019-05, Vol.21 (9), p.3153-3157
Main Authors: Mao, Peng-Fei, Zhou, Li-Jin, Zheng, An-Qi, Miao, Chun-Bao, Yang, Hai-Tao
Format: Article
Language:English
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Summary:A Cu­(OAc)2-promoted cascade reaction of malonate-tetherd acyl oximes with indoles, indole-2-alcohols, or indole-2-carboxmides provides facile access to polysubstituted 3-pyrrolin-2-ones. The reaction features the generation of two adjacent electrophilic centers at the same time as cyclization to lactam. The subsequent double addition with nucleophiles followed by oxidation realizes the difunctionalization of the imine sp2-carbon and the adjacent α-sp3-carbon.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00849