Sequential Amino-Claisen Rearrangement/Intramolecular 1,3-Dipolar ­Cycloaddition/Reductive Cleavage Approach to the Stereoselective Synthesis of cis-4-Hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines

Abstract A novel stereoselective synthesis of CIS-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-ben...

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Bibliographic Details
Published in:Synlett 2006-09, Vol.2006 (14), p.2275-2277
Main Authors: Gómez Ayala, Sandra Liliana, Stashenko, Elena, Palma, Alirio, Bahsas, Alí, Amaro-Luis, Juan Manuel
Format: Article
Language:English
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Summary:Abstract A novel stereoselective synthesis of CIS-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-benzylanilines followed by amino-Claisen rearrangement, subsequent oxidation with in situ 1,3-dipolar cycloaddition affording isoxazolidines, and finally reductive cleavage of the isoxazolidinic N-O bond.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-949654