title: Catalytic asymmetric allylation of 3,4-dihydroisoquinolines and its application to the synthesis of isoquinoline alkaloids.
abstract: A catalytic asymmetric allylation of 3,4-dihydroisoquinoline was carried out with allyltrimethoxylsilane-Cu as the nucleophile in the presence of DTBM-SEGPHOS as the chiral ligand to afford corresponding chiral 1-allyltetrahydroisoquinoline derivatives in good yield and stereoselectivity. The allyl adduct thus obtained was applied to the synthesis of several isoquinoline alkaloids such as crispine A and homolaudanosine. The reaction was further used for the synthesis of the isoquinoline moiety of schulzeine A.
authors.affiliation: School of Pharmacy, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
authors.forename: Michiko
authors.initials: M
authors.lastname: Miyazaki
authors.forename: Nami
authors.initials: N
authors.lastname: Ando
authors.forename: Keita
authors.initials: K
authors.lastname: Sugai
authors.forename: Yuki
authors.initials: Y
authors.lastname: Seito
authors.forename: Hiromi
authors.initials: H
authors.lastname: Fukuoka
authors.forename: Takuya
authors.initials: T
authors.lastname: Kanemitsu
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Nagata
authors.forename: Yuki
authors.initials: Y
authors.lastname: Odanaka
authors.forename: Kazuo T
authors.initials: KT
authors.lastname: Nakamura
authors.forename: Takashi
authors.initials: T
authors.lastname: Itoh
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C109852:G 1616; D007546:Isoquinolines; D008024:Ligands; D017646:Organosilicon Compounds; D003300:Copper