Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates
The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2007-03, Vol.72 (7), p.2674-2677 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2677 |
|---|---|
| container_issue | 7 |
| container_start_page | 2674 |
| container_title | Journal of organic chemistry |
| container_volume | 72 |
| creator | Cheng, Hsiu-Yi Sun, Chong-Si Hou, Duen-Ren |
| description | The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in good regioselectivities and high yields. Synthetic application in preparing N-tosyl-3-oxo-piperidine is also reported. |
| doi_str_mv | 10.1021/jo0624896 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_70299340</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>70299340</sourcerecordid><originalsourceid>FETCH-LOGICAL-a447t-2a908a32a9867f2ca50c7512a468029e5069b78964d95390f9f1a5937412c75d3</originalsourceid><addsrcrecordid>eNpt0M9PFDEUB_CGaGAFD_wDZC6aeBjt706PZCOsCVECq3JrHp03ZKCzhXbGuP71FnfDXuzlHfrJN-99CTlm9COjnH26j1Rz2Vi9R2ZMcVprS-UrMqOU81pwLQ7Im5zvaXlKqX1ywIyQQrJmRn5e4V0fMwb0Y_8Lq0sIAdp-Guo5jBDWf7CtzmIaYMTqCtupqLiqYld9rRc4Yop-7UPvq9MQ1v-mx7HYfERedxAyvt3OQ_L97PNyvqgvvp1_mZ9e1CClGWsOljYgymi06bgHRb1RjIPUDeUWFdX21pTLZGuVsLSzHQNlhZGMF9iKQ_J-k_uY4tOEeXRDnz2WI1YYp-xMSbFC0gI_bKBPMeeEnXtM_QBp7Rh1zy26lxaLPdmGTrcDtju5ra2Ad1sA2UPoEqx8n3eu0VpK-RxUb1yfR_z98g_pwWkjjHLLy2v34-b8Zt4sF26xywWfyz5TWpXu_rPgX7rgk1I</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>70299340</pqid></control><display><type>article</type><title>Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates</title><source>American Chemical Society Journals</source><creator>Cheng, Hsiu-Yi ; Sun, Chong-Si ; Hou, Duen-Ren</creator><creatorcontrib>Cheng, Hsiu-Yi ; Sun, Chong-Si ; Hou, Duen-Ren</creatorcontrib><description>The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in good regioselectivities and high yields. Synthetic application in preparing N-tosyl-3-oxo-piperidine is also reported.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0624896</identifier><identifier>PMID: 17343418</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 only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2007-03, Vol.72 (7), p.2674-2677</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-2a908a32a9867f2ca50c7512a468029e5069b78964d95390f9f1a5937412c75d3</citedby><cites>FETCH-LOGICAL-a447t-2a908a32a9867f2ca50c7512a468029e5069b78964d95390f9f1a5937412c75d3</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/jo0624896$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0624896$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18664446$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17343418$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cheng, Hsiu-Yi</creatorcontrib><creatorcontrib>Sun, Chong-Si</creatorcontrib><creatorcontrib>Hou, Duen-Ren</creatorcontrib><title>Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in good regioselectivities and high yields. Synthetic application in preparing N-tosyl-3-oxo-piperidine is also reported.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n 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>2007</creationdate><recordtype>article</recordtype><recordid>eNpt0M9PFDEUB_CGaGAFD_wDZC6aeBjt706PZCOsCVECq3JrHp03ZKCzhXbGuP71FnfDXuzlHfrJN-99CTlm9COjnH26j1Rz2Vi9R2ZMcVprS-UrMqOU81pwLQ7Im5zvaXlKqX1ywIyQQrJmRn5e4V0fMwb0Y_8Lq0sIAdp-Guo5jBDWf7CtzmIaYMTqCtupqLiqYld9rRc4Yop-7UPvq9MQ1v-mx7HYfERedxAyvt3OQ_L97PNyvqgvvp1_mZ9e1CClGWsOljYgymi06bgHRb1RjIPUDeUWFdX21pTLZGuVsLSzHQNlhZGMF9iKQ_J-k_uY4tOEeXRDnz2WI1YYp-xMSbFC0gI_bKBPMeeEnXtM_QBp7Rh1zy26lxaLPdmGTrcDtju5ra2Ad1sA2UPoEqx8n3eu0VpK-RxUb1yfR_z98g_pwWkjjHLLy2v34-b8Zt4sF26xywWfyz5TWpXu_rPgX7rgk1I</recordid><startdate>20070330</startdate><enddate>20070330</enddate><creator>Cheng, Hsiu-Yi</creator><creator>Sun, Chong-Si</creator><creator>Hou, Duen-Ren</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070330</creationdate><title>Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates</title><author>Cheng, Hsiu-Yi ; Sun, Chong-Si ; Hou, Duen-Ren</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-2a908a32a9867f2ca50c7512a468029e5069b78964d95390f9f1a5937412c75d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cheng, Hsiu-Yi</creatorcontrib><creatorcontrib>Sun, Chong-Si</creatorcontrib><creatorcontrib>Hou, Duen-Ren</creatorcontrib><collection>Istex</collection><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>Cheng, Hsiu-Yi</au><au>Sun, Chong-Si</au><au>Hou, Duen-Ren</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2007-03-30</date><risdate>2007</risdate><volume>72</volume><issue>7</issue><spage>2674</spage><epage>2677</epage><pages>2674-2677</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in good regioselectivities and high yields. Synthetic application in preparing N-tosyl-3-oxo-piperidine is also reported.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17343418</pmid><doi>10.1021/jo0624896</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2007-03, Vol.72 (7), p.2674-2677 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70299340 |
| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T08%3A08%3A42IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regioselective%20Palladium-Catalyzed%20Formate%20Reduction%20of%20N-Heterocyclic%20Allylic%20Acetates&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Cheng,%20Hsiu-Yi&rft.date=2007-03-30&rft.volume=72&rft.issue=7&rft.spage=2674&rft.epage=2677&rft.pages=2674-2677&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo0624896&rft_dat=%3Cproquest_cross%3E70299340%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=70299340&rft_id=info:pmid/17343418&rfr_iscdi=true |