Asymmetric Domino Heck/Dearomatization Reaction of β‑Naphthols to Construct Indole–Terpenoid Frameworks

A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole–terpenoid frameworks. This method affords indole-functionalize...

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Bibliographic Details
Published in:Organic letters 2021-10, Vol.23 (20), p.7865-7872
Main Authors: Wang, Dong-Chao, Cheng, Peng-Peng, Yang, Ting-Ting, Wu, Pan-Pan, Qu, Gui-Rong, Guo, Hai-Ming
Format: Article
Language:English
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Summary:A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole–terpenoid frameworks. This method affords indole-functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center in excellent yields (up to 92%) and enantioselectivities (up to 94% ee). In addition, the utility of this method is showcased by the gram-scale syntheses and diverse transformations of the dearomatized products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02881