title: Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.
abstract: With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a β-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Xiaochen
authors.initials: X
authors.lastname: Wang
authors.forename: Xinfang
authors.initials: X
authors.lastname: Xu
authors.forename: Peter Y
authors.initials: PY
authors.lastname: Zavalij
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D009589:Nitrogen Oxides; D009942:Organometallic Compounds; D010078:Oxazines; D014753:Vinyl Compounds; C015388:nitrones; C516829:vinylcarbene; D012238:Rhodium