Pd-Catalyzed Asymmetric Annulative Dearomatization of Phenols for Regio- and Enantioselective Synthesis of Spirocyclohexadienones
Hui‐Lin Mao, Yuxin Wang, Xue Wang, Haiying Wang, Wen‐Juan Hao, Bo Jiang
Abstract
A palladium-catalyzed asymmetric annulative dearomatization of phenols with butene dicarbonate is reported, enabling twofold decarboxylative allylation to regioselectively produce a range of spirocyclohexadienones with 29-95% yields and 74-99% ee. A catalytic dearomative formal [4 + 2] cyclization of 1,1'-biphenyl-2,4'-diols delivered spiro[chromane-4,1'-cyclohexane]-2',5'-dien-4'-ones with high enantioselectivity, whereas enantioenriched spiro[cyclohexane-1,4'-quinoline]-2,5-dien-4-ones were generated starting from 2'-amino-[1,1'-biphenyl]-4-ols as 1,4-dinucleophiles.
Topics & Concepts
ChemistryEnantioselective synthesisCatalysisCyclohexanePhenolsQuinolineBiphenylOrganic chemistryStereochemistryMedicinal chemistryCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions