title: Stereoselective synthesis of hydroxylated 3-aminoazepanes using a multi-bond forming, three-step tandem process.
abstract: A multi-bond forming, three-step tandem process involving a palladium(II)-catalysed Overman rearrangement and a ring closing metathesis reaction has been utilised for the efficient synthesis of a 2,3,6,7-tetrahydro-3-amidoazepine. Substrate directed epoxidation or dihydroxylation of this synthetic intermediate has allowed the diastereoselective synthesis of hydroxylated 3-aminoazepanes including the syn-diastereomer of the balanol core. Asymmetric synthesis of the 2,3,6,7-tetrahydro-3-amidoazepine motif was also achieved using a chiral palladium(II)-catalyst during the Overman rearrangement.
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, UK.
authors.forename: Sajjad
authors.initials: S
authors.lastname: Ahmad
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001381:Azepines; D010165:Palladium