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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Alkenes / chemistry*
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Amination
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Amino Alcohols / chemical synthesis*
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Amino Alcohols / chemistry*
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Carbamates / chemical synthesis*
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Carbamates / chemistry*
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Catalysis
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Cyclization
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Indicators and Reagents / chemistry
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Magnetic Resonance Spectroscopy
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Oxazolidinones / chemical synthesis*
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Oxazolidinones / chemistry*
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Stereoisomerism
Substances
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Alkenes
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Amino Alcohols
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Carbamates
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Indicators and Reagents
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Oxazolidinones
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trans-1-bromo-2-N-bis-carbamate