An Enantioselective Access to
1-Alkyl-1,2,3,4-tetrahydroisoquinolines. Application to a New
Synthesis of (−)-Argemonine<sup>†</sup>
Jean-Jacques Youte
Denis Barbier
Ali Al-Mourabit
Dino Gnecco
Christian Marazano
10.1021/jo0357869.s001
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
Potassium ferricyanide oxidation of salt <b>1 </b>gave isoquinolinone <b>7 </b>whose treatment with Grignard
reagents resulted in a high-yield formation of substituted isoquinolinium salts <b>5</b>. The selectivity of
the reduction of these salts to give derivatives <b>6</b> 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.
2004-04-16 00:00:00
benzylic group
New Synthesis
Grignard reagents
derivatives 6
isoquinolinium salts 5
enantioselective synthesis
isoquinolinone 7
Enantioselective Access
salt 1