<i>N</i>-Iodosuccinimide-Mediated Dimerization of 2-Alkynylnaphthols: A Highly Diastereoselective Construction of Bridged Polycyclic Compounds via Vinylidene <i>ortho</i>-Quinone Methide Intermediate
Yu Tan, Zhengxing Zhao, Zhili Chen, Sheng‐Li Huang, Shiqi Jia, Lei Peng, Da Xu, Wenling Qin, Hailong Yan
Abstract
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 N-iodosuccinimide as a promoter, simultaneously constructing one new C–O bond and two new C–C bonds. A tetra-substituted vinylidene ortho-quinone methide intermediate was likely involved, and the steric hindrance of substituents played a critical role in this transformation.
Topics & Concepts
ChemistrySteric effectsQuinone methideMoietyOctaneStereochemistryBicyclic moleculeQuinoneMedicinal chemistryCombinatorial chemistryOrganic chemistrySynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacology