Enantioselective Synthesis of Isoindolinone by Palladium-Catalyzed Aminoalkynylation of <i>O</i>-Phenyl Hydroxamic Ethers with Alkynes
Lei Wang, Yinqiang Wang, Shuaijie Wu, Chao‐Guo Yan, Chaoshen Zhang, Junliang Zhang, Ying Han
Abstract
-phenyl hydroxamic ethers with terminal alkynes is described. This protocol enables versatile access to challenging chiral isoindolinone derivatives bearing a quaternary stereogenic center. The palladium-catalyzed aminoalkynylation reaction shows broad functional group tolerance and allows the straightforward preparation of isoindolinones with high efficiency and excellent enantioselectivity under mild conditions. DFT calculations were performed to disclose the reaction mechanism and the origins of the enantioselectivity.
Topics & Concepts
ChemistryStereocenterCatalysisPalladiumEnantioselective synthesisFunctional groupSonogashira couplingCombinatorial chemistryHydroxamic acidOrganic chemistryPolymerSynthesis and pharmacology of benzodiazepine derivativesSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic Chemistry