title: Organocatalytic [4 + 2] cyclocondensation of α,β-unsaturated acyl chlorides with imines: highly enantioselective synthesis of dihydropyridinone and piperidine derivatives.
abstract: The cinchona alkaloid-catalyzed [4 + 2] cyclocondensation of α,β-unsaturated acyl chlorides with imines is developed to give the corresponding substituted dihydropyridinones in good yields with high to excellent enantioselectivities. Reduction of the dihydropyridinones gave highly optically active substituted tetrahydropyridinone and piperidine derivatives.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. songye@iccas.ac.cn.
authors.forename: Wen-Qiang
authors.initials: WQ
authors.lastname: Jia
authors.forename: Xiang-Yu
authors.initials: XY
authors.lastname: Chen
authors.forename: Li-Hui
authors.initials: LH
authors.lastname: Sun
authors.forename: Song
authors.initials: S
authors.lastname: Ye
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D003500:Cyclization; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D004095:Dihydropyridines; D006843:Hydrocarbons, Chlorinated; D007097:Imines; D010880:Piperidines; D011728:Pyridones