Asymmetric Hydrogenation of 2-Aryl-3-phthalimidopyridinium Salts: Synthesis of Piperidine Derivatives with Two Contiguous Stereocenters
Long‐Sheng Zheng, Fangyuan Wang, Xiang-Yu Ye, Gen‐Qiang Chen, Xumu Zhang
Abstract
Asymmetric hydrogenation of 2-aryl-3-phthalimidopyridinium salts catalyzed by the Ir/SegPhos catalytic system was described, leading to the corresponding chiral piperidine derivatives bearing two contiguous chiral centers, with high levels of enantioselectivities and diastereoselectivities. A gram-scale experiment has demonstrated the utility of this approach. The phthaloyl group could be easily removed and then smoothly converted to key intermediate (+)-CP-99994 as one of the neurokinin 1 receptor antagonists.
Topics & Concepts
ChemistryStereocenterPiperidineArylAsymmetric hydrogenationCatalysisEnantioselective synthesisCombinatorial chemistryStereochemistryOrganic chemistryAlkylAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisAsymmetric Synthesis and Catalysis