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

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 underwe...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-02, Vol.80 (3), p.1440-1445
Main Authors: Kuszpit, Michael R, Giletto, Matthew B, Jones, Corey L, Bethel, Travis K, Tepe, Jetze J
Format: Article
Language:English
Subjects:
alkenes
Alkenes - chemistry
Amination
amino alcohols
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Carbamates - chemical synthesis
Carbamates - chemistry
Catalysis
chemical reactions
Cyclization
Indicators and Reagents - chemistry
Magnetic Resonance Spectroscopy
organic chemistry
Oxazolidinones - chemical synthesis
Oxazolidinones - chemistry
Stereoisomerism
stereoisomers
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo502369d