title: Hydroxyamination of olefins using Br-N-(CO2Me)2.
abstract: The hydroxyamination reagent Br-N-(CO2Me)2 underwent Markovnikov addition to various olefins in the presence of catalytic BF3·OEt2 and provides efficient access to aminoalcohols. The reaction provided the trans-1-bromo, 2-N-bis-carbamate adduct stereoisomer in all cases. The resulting adduct underwent cyclization to give an oxazolidinone, which could be readily hydrolyzed to an oxazolidin-2-one or an amino alcohol.
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Michael R
authors.initials: MR
authors.lastname: Kuszpit
authors.forename: Matthew B
authors.initials: MB
authors.lastname: Giletto
authors.forename: Corey L
authors.initials: CL
authors.lastname: Jones
authors.forename: Travis K
authors.initials: TK
authors.lastname: Bethel
authors.forename: Jetze J
authors.initials: JJ
authors.lastname: Tepe
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000605:Amino Alcohols; D002219:Carbamates; D007202:Indicators and Reagents; D023303:Oxazolidinones; C000600231:trans-1-bromo-2-N-bis-carbamate