An Enantioselective Access to 1-Alkyl-1,2,3,4-tetrahydroisoquinolines. Application to a New Synthesis of (−)-Argemonine

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 (8...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-04, Vol.69 (8), p.2737-2740
Main Authors: Youte, Jean-Jacques, Barbier, Denis, Al-Mourabit, Ali, Gnecco, Dino, Marazano, Christian
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0357869