Nickel(<scp>ii</scp>)-catalyzed asymmetric thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles
Wei Yang, Xiaobin Lin, Yongyan Zhang, Weidi Cao, Xiaohua Liu, Xiaoming Feng
Abstract
A nickel(ii) catalyzed enantioselective thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles was realized with modified chiral N,N'-dioxide ligands, affording a variety of C3-substituted indole derivatives in high yields (up to 95%) with excellent enantioselectivities (up to 96% ee) under mild reaction conditions. A possible transition state model was proposed based on previous reports and the X-ray crystal structure of the catalyst.
Topics & Concepts
DiazoClaisen rearrangementThio-Carroll rearrangementNickelCatalysisChemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods