Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones <i>via</i> direct sulfide-catalyzed [2 + 1] annulation of <i>para</i>-quinone methides with bromides
Yingpeng Su, Ya‐Nan Zhao, Bingbing Chang, Qinqin Ling, Yawei Feng, Xiaolong Zhao, Danfeng Huang, Ke‐Hu Wang, Congde Huo, Yulai Hu
Abstract
An efficient sulfide-catalyzed [2 + 1] annulation of para-quinone methides (p-QMs) with diverse bromides has been achieved. This catalytic strategy provides an efficient and straightforward protocol for accessing a variety of spiro-cyclopropanyl-cyclohexadienone compounds in good to excellent yields (64% to 96% yields) with outstanding diastereoselectivities (>20 : 1 dr), displaying good functional group tolerance as well as gram-scale capacity.
Topics & Concepts
AnnulationChemistryQuinoneCatalysisSulfideMedicinal chemistryCombinatorial chemistryOrganic chemistrySynthesis of Indole DerivativesSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions