Catalytic Asymmetric Decarboxylative Michael Addition To Construct an All-Carbon Quaternary Center with 3-Alkenyl-oxindoles
Ying‐Zheng Ren, Shuhui Lu, Lin He, Zhifei Zhao, Shiwu Li
Abstract
The first highly enantioselective asymmetric decarboxylative addition of β-keto acids with 3-alkenyl-oxindoles bearing an all-carbon quaternary stereocenter have been developed. The relevant products were acquired in 49-98% yields with 88-98% enantioselectivities in the presence of 0.04-1.0 mol % of chiral rhodium catalyst. The comprehensive practicability of this method was proven in the preparation of the key intermediate, which can be easily transformed into analogues of physovenine and physostigmine.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisQuaternary carbonCatalysisRhodiumMichael reactionCarbon fibersOrganic chemistryStereochemistryMaterials scienceComposite numberComposite materialAsymmetric Synthesis and CatalysisChemical synthesis and alkaloidsAsymmetric Hydrogenation and Catalysis