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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.

SUBMITTER: Kuszpit MR

PROVIDER: S-EPMC5720370 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Hydroxyamination of olefins using Br-N-(CO2Me)2.

Kuszpit Michael R MR Giletto Matthew B MB Jones Corey L CL Bethel Travis K TK Tepe Jetze J JJ

The Journal of organic chemistry 20150122 3

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. ...[more]

PMID: 25574949

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