title: Enantioselective synthesis of indoloquinolizidines via asymmetric catalytic hydrogenation/lactamization of imino diesters.
abstract: We have developed a highly efficient cascade sequence for asymmetric synthesis of indoloquinolizidines with absolute control of cis-H2/H12b relative geometry in good to excellent yields and excellent enantioselectivities. This cascade was triggered by the Ru(II)-TsDPEN-catalyzed asymmetric transfer hydrogenation of imino diesters, with subsequent spontaneous lactamization with discrimination between the two diastereotopic 2-alkoxy-2-oxoethyl groups. The synthetic utility of this strategy was demonstrated by the asymmetric preparation of dihydrocorynantheol, geissoschizol, and isogeissoschizol.
authors.affiliation: Department of Chemistry, Shanghai University , 99 Shangda Road, Shanghai 200444, People's Republic of China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Liu
authors.forename: Qun
authors.initials: Q
authors.lastname: Wang
authors.forename: Ying
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jianbiao
authors.initials: J
authors.lastname: Huang
authors.forename: Linlin
authors.initials: L
authors.lastname: Nie
authors.forename: Jie
authors.initials: J
authors.lastname: Chen
authors.forename: Weiguo
authors.initials: W
authors.lastname: Cao
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Wu
mesh_terms: D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006865:Hydrogenation; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007097:Imines; D009942:Organometallic Compounds; D054837:Quinolizidines