title: Enantio- and diastereoselective synthesis of highly substituted benzazepines by a multicomponent strategy coupled with organocatalytic and enzymatic procedures.
abstract: Enantiomerically pure 4,5-dihydro-1H-benzo[c]azepines with three contiguous stereogenic centers have been assembled by convergent strategy with a good control of diastereoselectivity. The two steps are as follows: an asymmetric organocatalytic Mannich reaction performed on Boc-imines of o-(azidomethyl)benzaldehydes, followed by a one-pot Staudinger/aza-Wittig/Ugi-Joullié sequence. The latter reaction represents one of the first examples of diastereoselective Ugi three-component reaction on a seven-membered cyclic imine. The o-azidomethylbenzaldehydes have been synthesized employing a simple and efficient chemoenzymatic strategy from commercially available building blocks.
authors: Department of Chemistry and Industrial Chemistry, University of Genova , Via Dodecaneso, 31, 16146 Genova, Italy.
authors: Lisa
authors: L
authors: Moni
authors: Luca
authors: L
authors: Banfi
authors: Andrea
authors: A
authors: Basso
authors: Andrea
authors: A
authors: Galatini
authors: Martina
authors: M
authors: Spallarossa
authors: Renata
authors: R
authors: Riva
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D001552:Benzazepines; D007097:Imines