90192-90-8Relevant academic research and scientific papers
Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes
Huang, Tianyu,Liu, Xiaohua,Lang, Jiawen,Xu, Jian,Lin, Lili,Feng, Xiaoming
, p. 5654 - 5660 (2017)
An efficient asymmetric aerobic oxidation of tetrahydroisoquinolines with terminal alkynes was realized under mild reaction conditions using O2 as the sole oxidant. A chiral N,N′-dioxide/zinc(II)/iron(II) bimetallic cooperative catalytic system
Catalytic asymmetric alkynylation of C1-substituted C,N-cyclic azomethine imines by CuI/chiral bronsted acid co-catalyst
Hashimoto, Takuya,Omote, Masato,Maruoka, Keiji
, p. 8952 - 8955 (2011/10/31)
It all adds up: The title reaction was developed for the synthesis of chiral tetrahydroisoquinoline derivatives with a tetrasubstituted carbon center at the C1-position (see scheme, Bz=benzoyl, pybox=2,6-bis(2-oxazolinyl)pyridine) . The reaction was facilitated effectively by the co-catalyst system composed of copper(I)/Ph-pybox and an axially chiral dicarboxylic acid.
Asymmetric addition of nucleophiles to C-1 position of isoquinolines using (S)-alanine derivatives as chiral auxiliaries
Itoh, Takashi,Nagata, Kazuhiro,Miyazaki, Michiko,Kameoka, Keiko,Ohsawa, Akio
, p. 8827 - 8839 (2007/10/03)
5,8-Dibromoisoquinoline derivatives were allowed to react with a nucleophile (silyl enol ether or allyltributyltin) in the presence of an acyl chloride derived from (S)-alanine to afford the 1,2-addition products in good chemical yields and high stereoselectivity. The bromo groups were readily removed by a reduction process in which the double bond at C3-C4 was also reduced. Thus the reaction system provided a general method to synthesize asymmetric 1-substituted tetrahydroisoquinolines. In order to determine the absolute configuration of the reaction product, (-)-homolaudanosine was synthesized in an enantiopure form. The stereoselectivity was rationally understood from the conformation of intermediary N-acylated isoquinolinium salts.
