title: Enantioselective double manipulation of tetrahydroisoquinolines with terminal alkynes and aldehydes under copper(I) catalysis.
abstract: Tetrahydroisoquinoline alkaloids with a C1 stereogenic center are a common unit in many natural and non-natural compounds of biological importance. Herein we describe a novel Cu(I) -catalyzed highly chemo- and enantioselective synthesis of chiral tetrahydroisoquinoline-alkaloid derivatives from readily available unsubstituted tetrahydroisoquinolines, aldehydes, and terminal alkynes in the presence of the ligand (R,R)-N-pinap. This synthetic operation installs two substituents in the 1- and 2-positions.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China).
authors.forename: Weilong
authors.initials: W
authors.lastname: Lin
authors.forename: Tao
authors.initials: T
authors.lastname: Cao
authors.forename: Wu
authors.initials: W
authors.lastname: Fan
authors.forename: Yulin
authors.initials: Y
authors.lastname: Han
authors.forename: Jinqiang
authors.initials: J
authors.lastname: Kuang
authors.forename: Hongwen
authors.initials: H
authors.lastname: Luo
authors.forename: Bukeyan
authors.initials: B
authors.lastname: Miao
authors.forename: Xinjun
authors.initials: X
authors.lastname: Tang
authors.forename: Qiong
authors.initials: Q
authors.lastname: Yu
authors.forename: Weiming
authors.initials: W
authors.lastname: Yuan
authors.forename: Jiasheng
authors.initials: J
authors.lastname: Zhang
authors.forename: Can
authors.initials: C
authors.lastname: Zhu
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D007546:Isoquinolines; D003300:Copper
keywords: alkynylation; asymmetric catalysis; chirality; copper; tetrahydroisoquinoline alkaloids