Synthesis of Octahydroquinolines through the Lewis Acid Catalyzed Reaction of Vinyl Allenes and Imines

The reaction of vinyl allenes with imines under Lewis acid catalysis has been explored. Vinyl allenes in which the allenic portion of the molecule is tri- or tetrasubstituted gave octahydroquinoline derivatives as single isomers together with a minor compound formed by an ene reaction of the imine w...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-10, Vol.68 (20), p.7845-7852
Main Authors: Regás, David, Afonso, María M, Rodríguez, Matías L, Palenzuela, J. Antonio
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:The reaction of vinyl allenes with imines under Lewis acid catalysis has been explored. Vinyl allenes in which the allenic portion of the molecule is tri- or tetrasubstituted gave octahydroquinoline derivatives as single isomers together with a minor compound formed by an ene reaction of the imine with the allene. Compounds in which the allene is 1,3-disubstituted do not react under the conditions assayed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034480z