%0 Journal Article
%A Youte, Jean-Jacques
%A Barbier, Denis
%A Al-Mourabit, Ali
%A Gnecco, Dino
%A Marazano, Christian
%D 2004
%T An Enantioselective Access to
1-Alkyl-1,2,3,4-tetrahydroisoquinolines. Application to a New
Synthesis of (−)-Argemonine†
%U https://acs.figshare.com/articles/journal_contribution/An_Enantioselective_Access_to_1_Alkyl_1_2_3_4_tetrahydroisoquinolines_Application_to_a_New_Synthesis_of_Argemonine_sup_sup_/3342679
%R 10.1021/jo0357869.s001
%2 https://ndownloader.figshare.com/files/5181892
%K benzylic group
%K New Synthesis
%K Grignard reagents
%K derivatives 6
%K isoquinolinium salts 5
%K enantioselective synthesis
%K isoquinolinone 7
%K Enantioselective Access
%K salt 1
%X Potassium ferricyanide oxidation of salt 1 gave isoquinolinone 7 whose treatment with Grignard
reagents resulted in a high-yield formation of substituted isoquinolinium salts 5. The selectivity of
the reduction of these salts to give derivatives 6 has been studied. Particularly good selectivities
(82−84%) were observed when R is a benzylic group. On the basis of these results, a practical and
enantioselective synthesis of the natural alkaloid (−)-argemonine is presented.
%I ACS Publications