29268-20-0Relevant academic research and scientific papers
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 (2001)
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.
