1,7-Asymmetric induction in a nitrogen ring expansion process facilitated by in situ tethering.
[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.
Furness
K
K
Department of Medicinal Chemistry, University of Kansas, Lawrence 66045-2506, USA.
Aubé
J
J
D002209:Caprolactam / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003512:Cyclohexanones / Q000737:chemistry*; D009584:Nitrogen; D013237:Stereoisomerism
D003512:Cyclohexanones; D002209:Caprolactam; D009584:Nitrogen