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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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| Published in: | Journal of organic chemistry 2015-02, Vol.80 (3), p.1440-1445 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a353d-d1589f96f9a6bcfd4aae617dfe96e5a8954f9a61783d2f29816bc1a03d57bf503 |
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| cites | cdi_FETCH-LOGICAL-a353d-d1589f96f9a6bcfd4aae617dfe96e5a8954f9a61783d2f29816bc1a03d57bf503 |
| container_end_page | 1445 |
| container_issue | 3 |
| container_start_page | 1440 |
| container_title | Journal of organic chemistry |
| container_volume | 80 |
| creator | Kuszpit, Michael R Giletto, Matthew B Jones, Corey L Bethel, Travis K Tepe, Jetze J |
| description | 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. |
| doi_str_mv | 10.1021/jo502369d |
| format | article |
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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.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo502369d</identifier><identifier>PMID: 25574949</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>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</subject><ispartof>Journal of organic chemistry, 2015-02, Vol.80 (3), p.1440-1445</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a353d-d1589f96f9a6bcfd4aae617dfe96e5a8954f9a61783d2f29816bc1a03d57bf503</citedby><cites>FETCH-LOGICAL-a353d-d1589f96f9a6bcfd4aae617dfe96e5a8954f9a61783d2f29816bc1a03d57bf503</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25574949$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kuszpit, Michael R</creatorcontrib><creatorcontrib>Giletto, Matthew B</creatorcontrib><creatorcontrib>Jones, Corey L</creatorcontrib><creatorcontrib>Bethel, Travis K</creatorcontrib><creatorcontrib>Tepe, Jetze J</creatorcontrib><title>Hydroxyamination of Olefins Using Br-N-(CO2Me)2</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>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. 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Org. Chem</addtitle><date>2015-02-06</date><risdate>2015</risdate><volume>80</volume><issue>3</issue><spage>1440</spage><epage>1445</epage><pages>1440-1445</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25574949</pmid><doi>10.1021/jo502369d</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2015-02, Vol.80 (3), p.1440-1445 |
| issn | 0022-3263 1520-6904 1520-6904 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5720370 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| 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 |
| title | Hydroxyamination of Olefins Using Br-N-(CO2Me)2 |
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