682153-82-8Relevant articles and documents
An Enantioselective Access to 1-Alkyl-1,2,3,4-tetrahydroisoquinolines. Application to a New Synthesis of (-)-Argemonine
Youte, Jean-Jacques,Barbier, Denis,Al-Mourabit, Ali,Gnecco, Dino,Marazano, Christian
, p. 2737 - 2740 (2007/10/03)
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.