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-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.