title: 1,7-Asymmetric induction in a nitrogen ring expansion process facilitated by in situ tethering.
abstract: [formula: see text] There are only a few methods for the asymmetric ring expansion of prochiral ketones. Symmetrically substituted cyclohexanones can be converted to the corresponding ring-expanded caprolactam with excellent 1,7-diastereoselectivity (> or = 93% ds) and yields (> or = 86%), using a chiral hydroxy azide-mediated Schmidt reaction.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, Lawrence 66045-2506, USA.
authors.forename: K
authors.initials: K
authors.lastname: Furness
authors.forename: J
authors.initials: J
authors.lastname: Aubé
mesh_terms: D002209:Caprolactam / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003512:Cyclohexanones / Q000737:chemistry*; D009584:Nitrogen; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones; D002209:Caprolactam; D009584:Nitrogen