One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates
Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ri...
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| Veröffentlicht in: | Journal of organic chemistry 2010-11, Vol.75 (22), p.7745-7756 |
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| container_issue | 22 |
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| container_title | Journal of organic chemistry |
| container_volume | 75 |
| creator | Davies, Stephen G Fletcher, Ai M Kurosawa, Wataru Lee, James A Poce, Giovanna Roberts, Paul M Thomson, James E Williamson, David M |
| description | Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. When a solution of a secondary allylic or homoallylic amine and Br3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one). |
| doi_str_mv | 10.1021/jo101614f |
| format | Article |
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The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. When a solution of a secondary allylic or homoallylic amine and Br3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo101614f</identifier><identifier>PMID: 20954691</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2010-11, Vol.75 (22), p.7745-7756</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-a3c01b4452feaf9452c8e7f052214720a7a1d1baa2facc7e3853fa1d3417e0b33</citedby><cites>FETCH-LOGICAL-a345t-a3c01b4452feaf9452c8e7f052214720a7a1d1baa2facc7e3853fa1d3417e0b33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo101614f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo101614f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23531586$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20954691$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Davies, Stephen G</creatorcontrib><creatorcontrib>Fletcher, Ai M</creatorcontrib><creatorcontrib>Kurosawa, Wataru</creatorcontrib><creatorcontrib>Lee, James A</creatorcontrib><creatorcontrib>Poce, Giovanna</creatorcontrib><creatorcontrib>Roberts, Paul M</creatorcontrib><creatorcontrib>Thomson, James E</creatorcontrib><creatorcontrib>Williamson, David M</creatorcontrib><title>One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. When a solution of a secondary allylic or homoallylic amine and Br3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one).</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNptkF1LwzAUhoMoOqcX_gHpjaAX1Zx8tOvlKOqEwQT1upxmCVTaZCatsH9vxuYGYi5ycg4PTzgvIVdA74EyePh0QCEDYY7ICCSjaVZQcUxGlDKWcpbxM3IewieNR0p5Ss4YLaTIChiRYWF1-ur6pHT2W_vQOBsSZ5JFq00Tn71LyrVqG5WU6GtnsdchQbtM3rRydol-nUzbdr0BNtOZ6xzu-mnXWP3XgN3GcEFODLZBX-7qmHw8Pb6Xs3S-eH4pp_MUuZB9vBWFWgjJjEZTxKomOjdUMgYiZxRzhCXUiMygUrnmE8lNHHEBuaY152Nyu_WuvPsadOirrglKty1a7YZQgSgKgAnNIaJ3W1R5F4LXplr5pov7VUCrTcrVPuXIXu-0Q93p5Z78jTUCNzsAg8LWeLSqCQeOSw5ykh04VCH6B29jGv98-APBbpCY</recordid><startdate>20101119</startdate><enddate>20101119</enddate><creator>Davies, Stephen G</creator><creator>Fletcher, Ai M</creator><creator>Kurosawa, Wataru</creator><creator>Lee, James A</creator><creator>Poce, Giovanna</creator><creator>Roberts, Paul M</creator><creator>Thomson, James E</creator><creator>Williamson, David M</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20101119</creationdate><title>One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates</title><author>Davies, Stephen G ; Fletcher, Ai M ; Kurosawa, Wataru ; Lee, James A ; Poce, Giovanna ; Roberts, Paul M ; Thomson, James E ; Williamson, David M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-a3c01b4452feaf9452c8e7f052214720a7a1d1baa2facc7e3853fa1d3417e0b33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Davies, Stephen G</creatorcontrib><creatorcontrib>Fletcher, Ai M</creatorcontrib><creatorcontrib>Kurosawa, Wataru</creatorcontrib><creatorcontrib>Lee, James A</creatorcontrib><creatorcontrib>Poce, Giovanna</creatorcontrib><creatorcontrib>Roberts, Paul M</creatorcontrib><creatorcontrib>Thomson, James E</creatorcontrib><creatorcontrib>Williamson, David M</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Davies, Stephen G</au><au>Fletcher, Ai M</au><au>Kurosawa, Wataru</au><au>Lee, James A</au><au>Poce, Giovanna</au><au>Roberts, Paul M</au><au>Thomson, James E</au><au>Williamson, David M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-11-19</date><risdate>2010</risdate><volume>75</volume><issue>22</issue><spage>7745</spage><epage>7756</epage><pages>7745-7756</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. When a solution of a secondary allylic or homoallylic amine and Br3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20954691</pmid><doi>10.1021/jo101614f</doi><tpages>12</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates |
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