Palladium-Catalyzed Intermolecular Asymmetric Dearomative Annulation of Phenols with Vinyl Cyclopropanes
Wen‐Dao Chu, Tian-Tian Liang, Hao Ni, Zhi-Hong Dong, Zhihui Shao, Yong Liu, Cheng‐Yu He, Ruopeng Bai, Quan‐Zhong Liu
Abstract
Herein, we report the Pd(0)-catalyzed intermolecular asymmetric dearomative [3 + 2] annulation of phenols with vinyl cyclopropanes via in situ generated ortho-quinone methide intermediates. A series of highly functionalized spiro-[5,6] bicycles which bear three contiguous stereogenic centers including one all-carbon quaternary were obtained with excellent stereoselectivities. Density functional theory (DFT) calculations indicate that the reactions were controlled by thermodynamics.
Topics & Concepts
AnnulationStereocenterChemistryIntermolecular forcePhenolsCatalysisPalladiumDensity functional theoryOrganic chemistryCombinatorial chemistryMoleculeComputational chemistryEnantioselective synthesisSynthesis of Indole DerivativesCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques