Hydroxyamination of Olefins
Using Br-N-(CO2Me)2

Kuszpit, Michael
R.; Giletto, Matthew B.; Jones, Corey L.; Bethel, Travis K.; Tepe, Jetze J.

doi:10.1021/jo502369d.s001

jo502369d_si_001.pdf (3.42 MB)

Hydroxyamination of Olefins Using Br-N-(CO₂Me)₂

journal contribution

posted on 2015-02-06, 00:00 authored by Michael R. Kuszpit, Matthew B. Giletto, Corey L. Jones, Travis K. Bethel, Jetze J. Tepe

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.