N -Iodosuccinimide-Mediated Dimerization of 2-Alkynylnaphthols: A Highly Diastereoselective Construction of Bridged Polycyclic Compounds via Vinylidene ortho -Quinone Methide Intermediate

An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good to excellent yields. The reaction proceeded under mild conditions using -iodosuccinimide as a promoter, simultaneously...

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Bibliographic Details
Published in:Organic letters 2020-06, Vol.22 (11), p.4461-4466
Main Authors: Tan, Yu, Zhao, Zhengxing, Chen, Zhili, Huang, Shengli, Jia, Shiqi, Peng, Lei, Xu, Da, Qin, Wenling, Yan, Hailong
Format: Article
Language:English
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Summary:An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good to excellent yields. The reaction proceeded under mild conditions using -iodosuccinimide as a promoter, simultaneously constructing one new C-O bond and two new C-C bonds. A tetra-substituted vinylidene -quinone methide intermediate was likely involved, and the steric hindrance of substituents played a critical role in this transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01458