Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance
Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acy...
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| Veröffentlicht in: | Organic letters 2014-08, Vol.16 (15), p.4036-4039 |
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| creator | Du, Xiang-Wei Ghosh, Avipsa Stanley, Levi M |
| description | Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities. |
| doi_str_mv | 10.1021/ol501869s |
| format | Article |
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Lett</addtitle><description>Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.</description><subject>Aldehydes - chemistry</subject><subject>Alkenes - chemistry</subject><subject>Catalysis</subject><subject>Chelating Agents - chemistry</subject><subject>chelation</subject><subject>chemical structure</subject><subject>enantioselective synthesis</subject><subject>enantioselectivity</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>hydrides</subject><subject>Ketones - chemical synthesis</subject><subject>Ketones - chemistry</subject><subject>Letter</subject><subject>Molecular Structure</subject><subject>nitrogen</subject><subject>Nitrogen - chemistry</subject><subject>organic compounds</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>N~.</sourceid><sourceid>EIF</sourceid><recordid>eNqFkk2PFCEQhonRuB968A8YLiZ6aIVu6On2YDLprI7J-pFdPROgixlWBlagN9v-Jn-kTGadaGLiCfLy1FtFVSH0hJKXlNT0VXCc0K7t0z10THndVAvC6_uHe0uO0ElKV4TQovQP0VHNSV0i2DH6eealzzYkcKCzvQF8Ofu8gWQTDgZ_Dm7Ws3ZW4482x7AGj1eQIYadCgmrGV9sqkFm6eYfMOKl-wYe8GoeY5B6drJ4-9d4CD7lOJUMfo0v7W31AbYKYgm4KErC1uOSFC9VAq9hl3nYwD4YL1MpJsuiP0IPjHQJHt-dp-jr27Mvw6o6__Tu_bA8ryQnLFeUQ98SphfKtNCYGlrWL3opG0UMrSVpjOmpaVSrFNM174yWbcPVCEBaavqxOUVv9r7Xk9rCqMHnKJ24jnYr4yyCtOLvF283Yh1uBKOMLTgrBs_vDGL4PkHKYmuTBuekhzAlUZf296TraPdflHJeZtywlhT0xR7VMaQUwRwqokTsFkEcFqGwT__8woH8PfkCPNsDUidxFaboS0f_YfQLteG_ZA</recordid><startdate>20140801</startdate><enddate>20140801</enddate><creator>Du, Xiang-Wei</creator><creator>Ghosh, Avipsa</creator><creator>Stanley, Levi M</creator><general>American Chemical Society</general><scope>N~.</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20140801</creationdate><title>Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance</title><author>Du, Xiang-Wei ; Ghosh, Avipsa ; Stanley, Levi M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a504t-15e9604c7bf6e3f2e64979aa3b0f12a03ff91f3b6bb4c258fca635bdee061f9d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aldehydes - chemistry</topic><topic>Alkenes - chemistry</topic><topic>Catalysis</topic><topic>Chelating Agents - chemistry</topic><topic>chelation</topic><topic>chemical structure</topic><topic>enantioselective synthesis</topic><topic>enantioselectivity</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>hydrides</topic><topic>Ketones - chemical synthesis</topic><topic>Ketones - chemistry</topic><topic>Letter</topic><topic>Molecular Structure</topic><topic>nitrogen</topic><topic>Nitrogen - chemistry</topic><topic>organic compounds</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Du, Xiang-Wei</creatorcontrib><creatorcontrib>Ghosh, Avipsa</creatorcontrib><creatorcontrib>Stanley, Levi M</creatorcontrib><collection>American Chemical Society (ACS) Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Du, Xiang-Wei</au><au>Ghosh, Avipsa</au><au>Stanley, Levi M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2014-08-01</date><risdate>2014</risdate><volume>16</volume><issue>15</issue><spage>4036</spage><epage>4039</epage><pages>4036-4039</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25020184</pmid><doi>10.1021/ol501869s</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Organic letters, 2014-08, Vol.16 (15), p.4036-4039 |
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| source | ACS Publications; MEDLINE |
| subjects | Aldehydes - chemistry Alkenes - chemistry Catalysis Chelating Agents - chemistry chelation chemical structure enantioselective synthesis enantioselectivity Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry hydrides Ketones - chemical synthesis Ketones - chemistry Letter Molecular Structure nitrogen Nitrogen - chemistry organic compounds Rhodium - chemistry Stereoisomerism |
| title | Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance |
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