Highly Diastereoselective Synthesis of Oxindoles Containing Vicinal Quaternary and Tertiary Stereocenters by a Domino Heck/Decarboxylative Alkynylation Sequence
Dong‐Chao Wang, Panpan Wu, Peiyu Du, Gui‐Rong Qu, Hai‐Ming Guo
Abstract
A palladium-catalyzed domino Heck/decarboxylative alkynylation reaction of trisubstituted alkenes or enamines is reported. For two different types of substrates, the current domino reaction employing different solvents and bases led to 3,3-disubstituted oxindoles and hydropyrimidinyl spirooxindoles containing vicinal quaternary and tertiary stereocenters in moderate to good yields, respectively. The general applicability of this method was shown by gram-scale syntheses and diverse transformations of the reaction products. The enantioselective version for this domino process was also studied.
Topics & Concepts
StereocenterDominoChemistryVicinalEnantioselective synthesisHeck reactionCascade reactionAlkynylationCombinatorial chemistryPalladiumCatalysisOrganic chemistryStereochemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods