title: Kinetic resolution of 2-substituted 2,3-dihydro-4-pyridones by palladium-catalyzed asymmetric allylic alkylation: catalytic asymmetric total synthesis of indolizidine (-)-209I.
abstract: The kinetic resolution of 2-substituted-2,3-dihydro-4-pyridones was realized via a Pd-catalyzed allylic substitution reaction using a commercially available (S)-P-Phos as a ligand, affording optically active dihydropyridones and C-allylated dihydropyridones in high yields and good enantioselectivities with the S-factor up to 43. With this protocol, a catalytic asymmetric total synthesis of indolizidine (-)-209I was realized for the first time.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, ‡Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Bai-Lin
authors.initials: BL
authors.lastname: Lei
authors.forename: Qing-Song
authors.initials: QS
authors.lastname: Zhang
authors.forename: Wei-Hua
authors.initials: WH
authors.lastname: Yu
authors.forename: Qiu-Ping
authors.initials: QP
authors.lastname: Ding
authors.forename: Chang-Hua
authors.initials: CH
authors.lastname: Ding
authors.forename: Xue-Long
authors.initials: XL
authors.lastname: Hou
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000818:Animals; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry*; D011898:Ranidae; D012867:Skin / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D054836:Indolizidines; D011728:Pyridones; C000588839:indolizidine 209I; D010165:Palladium