title: Palladium-Catalyzed Asymmetric Allylic Allylation of Racemic Morita-Baylis-Hillman Adducts.
abstract: A palladium-catalyzed asymmetric allyl-allyl cross-coupling of acetates of racemic Morita-Baylis-Hillman adducts and allylB(pin) has been developed using a spiroketal-based bis(phosphine) as the chiral ligand, thus affording a series of chiral 1,5-dienes bearing a vinylic ester functionality in good yields, high branched regioselectivities, and uniformly excellent enantioselectivities (95-99 % ee). Further synthetic manipulations of the allylation products provided novel ways for rapid access to a range of chiral polycyclic lactones and polycyclic lactams, as well as the antidepressant drug (-)-Paroxetine, in high optical purities.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Xubin
authors.initials: X
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Zhaobin
authors.initials: Z
authors.lastname: Han
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, China.
authors.forename: Kuiling
authors.initials: K
authors.lastname: Ding
keywords: P ligands; allylic compounds; asymmetric catalysis; heterocycles; palladium