title: Carbamoyl anion addition to nitrones.
abstract: The addition of carbamoyl anions derived from N,N-disubstituted formamides and LDA to N-tert-butyl nitrones is described. The reaction was demonstrated with a variety of formamides and nitrones and provided a direct route to α-(N-hydroxy)amino amides. The use of a tert-leucinol derived chiral auxiliary on the nitrone provided products in good diastereoselectivity. Derivatization of the products by tert-butyl deprotection or N-deoxygenation was demonstrated.
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Chris
authors.initials: C
authors.lastname: Lorenc
authors.forename: Kaddy
authors.initials: K
authors.lastname: Camara
authors.forename: Zhibin
authors.initials: Z
authors.lastname: Li
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Carl A
authors.initials: CA
authors.lastname: Busacca
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D000838:Anions / Q000737:chemistry*; D005559:Formamides / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000838:Anions; D005559:Formamides; D009589:Nitrogen Oxides; C015388:nitrones; C417575:leucinol; D007930:Leucine