title: Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.
abstract: We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate beta-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Harit U
authors.initials: HU
authors.lastname: Vora
authors.forename: Johannah R
authors.initials: JR
authors.lastname: Moncecchi
authors.forename: Oleg
authors.initials: O
authors.lastname: Epstein
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D001386:Azides / Q000138:chemical synthesis*; D002384:Catalysis; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D001386:Azides; D010080:Oxazoles; C030011:carbene; D008697:Methane