%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