title: Urea-catalyzed construction of oxazinanes.
abstract: Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family of oxazinanes, typically in high yield. This method affords access to enantioenriched oxazinane products through chirality transfer from enantioenriched nitrocyclopropane carboxylates.
authors.affiliation: The Ohio State University, 100 W. 18th Ave., Columbus, OH, USA. mattson@chemistry.ohio-state.edu.
authors.forename: Andrea M
authors.initials: AM
authors.lastname: Hardman
authors.forename: Sonia S
authors.initials: SS
authors.lastname: So
authors.forename: Anita E
authors.initials: AE
authors.lastname: Mattson
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D014508:Urea / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D003521:Cyclopropanes; D009589:Nitrogen Oxides; D010078:Oxazines; C015388:nitrones; D014508:Urea