Catalytic Enantioselective Synthesis of Halocyclopropanes
A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocycloprop...
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| Veröffentlicht in: | Chemistry : a European journal 2016-04, Vol.22 (18), p.6239-6242 |
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| container_title | Chemistry : a European journal |
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| creator | Pons, Amandine Ivashkin, Pavel Poisson, Thomas Charette, André B. Pannecoucke, Xavier Jubault, Philippe |
| description | A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. The reported methodology represents the first general catalytic enantioselective approach to halocyclopropanes.
3‐Membered rings: Catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. |
| doi_str_mv | 10.1002/chem.201600649 |
| format | Article |
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3‐Membered rings: Catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201600649</identifier><identifier>PMID: 26945553</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Analytical chemistry ; asymmetric catalysis ; Asymmetry ; Catalysis ; Catalysts ; Chemical Sciences ; Cheminformatics ; Chemistry ; chiral rhodium catalyst ; cyclopropane ; diazo derivatives ; fluorine ; Medicinal Chemistry ; Methodology ; or physical chemistry ; Organic chemistry ; Rhodium ; Synthesis ; Theoretical and</subject><ispartof>Chemistry : a European journal, 2016-04, Vol.22 (18), p.6239-6242</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6519-f749ef13d75f9dbb5994b2b34ccd16f2982969d781d489df2de158032a5a3e23</citedby><cites>FETCH-LOGICAL-c6519-f749ef13d75f9dbb5994b2b34ccd16f2982969d781d489df2de158032a5a3e23</cites><orcidid>0000-0002-4598-7895 ; 0000-0002-3295-9326 ; 0000-0002-0503-9620</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201600649$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201600649$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26945553$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01321309$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Pons, Amandine</creatorcontrib><creatorcontrib>Ivashkin, Pavel</creatorcontrib><creatorcontrib>Poisson, Thomas</creatorcontrib><creatorcontrib>Charette, André B.</creatorcontrib><creatorcontrib>Pannecoucke, Xavier</creatorcontrib><creatorcontrib>Jubault, Philippe</creatorcontrib><title>Catalytic Enantioselective Synthesis of Halocyclopropanes</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. The reported methodology represents the first general catalytic enantioselective approach to halocyclopropanes.
3‐Membered rings: Catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios.</description><subject>Analytical chemistry</subject><subject>asymmetric catalysis</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical Sciences</subject><subject>Cheminformatics</subject><subject>Chemistry</subject><subject>chiral rhodium catalyst</subject><subject>cyclopropane</subject><subject>diazo derivatives</subject><subject>fluorine</subject><subject>Medicinal Chemistry</subject><subject>Methodology</subject><subject>or physical chemistry</subject><subject>Organic chemistry</subject><subject>Rhodium</subject><subject>Synthesis</subject><subject>Theoretical and</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqF0cFv0zAUBnALgVgZXDmiSlzgkGL7xXbecau6FSggxMSOluM4qocblzjdlv-eRBkV4rKTJev3Pj37I-Q1owtGKf9gt2634JRJSmWOT8iMCc4yUFI8JTOKucqkADwhL1K6oZSiBHhOTrjEXAgBM4JL05nQd97OV41pOh-TC852_tbNf_RNt3XJp3ms52sTou1tiPs27k3j0kvyrDYhuVcP5ym5ulhdLdfZ5tvlx-XZJrNSMMxqlaOrGVRK1FiVpUDMS15Cbm3FZM2x4CixUgWr8gKrmleOiYICN8KA43BK3k-xWxP0vvU70_Y6Gq_XZxs93lEGnAHFWzbYd5Mddvx9cKnTO5-sC2HYNx6SZgUtKApWqMepKgBg-K6Rvv2P3sRD2wxvHhVnHHJBB7WYlG1jSq2rj8syqseq9FiVPlY1DLx5iD2UO1cd-d9uBoATuPPB9Y_E6eV69eXf8Gya9alz98dZ0_7SUoES-vrrpT6_wO8_rz8p_Rn-AMo_rLQ</recordid><startdate>20160425</startdate><enddate>20160425</enddate><creator>Pons, Amandine</creator><creator>Ivashkin, Pavel</creator><creator>Poisson, Thomas</creator><creator>Charette, André B.</creator><creator>Pannecoucke, Xavier</creator><creator>Jubault, Philippe</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-4598-7895</orcidid><orcidid>https://orcid.org/0000-0002-3295-9326</orcidid><orcidid>https://orcid.org/0000-0002-0503-9620</orcidid></search><sort><creationdate>20160425</creationdate><title>Catalytic Enantioselective Synthesis of Halocyclopropanes</title><author>Pons, Amandine ; Ivashkin, Pavel ; Poisson, Thomas ; Charette, André B. ; Pannecoucke, Xavier ; Jubault, Philippe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6519-f749ef13d75f9dbb5994b2b34ccd16f2982969d781d489df2de158032a5a3e23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Analytical chemistry</topic><topic>asymmetric catalysis</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical Sciences</topic><topic>Cheminformatics</topic><topic>Chemistry</topic><topic>chiral rhodium catalyst</topic><topic>cyclopropane</topic><topic>diazo derivatives</topic><topic>fluorine</topic><topic>Medicinal Chemistry</topic><topic>Methodology</topic><topic>or physical chemistry</topic><topic>Organic chemistry</topic><topic>Rhodium</topic><topic>Synthesis</topic><topic>Theoretical and</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pons, Amandine</creatorcontrib><creatorcontrib>Ivashkin, Pavel</creatorcontrib><creatorcontrib>Poisson, Thomas</creatorcontrib><creatorcontrib>Charette, André B.</creatorcontrib><creatorcontrib>Pannecoucke, Xavier</creatorcontrib><creatorcontrib>Jubault, Philippe</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pons, Amandine</au><au>Ivashkin, Pavel</au><au>Poisson, Thomas</au><au>Charette, André B.</au><au>Pannecoucke, Xavier</au><au>Jubault, Philippe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Enantioselective Synthesis of Halocyclopropanes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-04-25</date><risdate>2016</risdate><volume>22</volume><issue>18</issue><spage>6239</spage><epage>6242</epage><pages>6239-6242</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. The reported methodology represents the first general catalytic enantioselective approach to halocyclopropanes.
3‐Membered rings: Catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26945553</pmid><doi>10.1002/chem.201600649</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4598-7895</orcidid><orcidid>https://orcid.org/0000-0002-3295-9326</orcidid><orcidid>https://orcid.org/0000-0002-0503-9620</orcidid></addata></record> |
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| subjects | Analytical chemistry asymmetric catalysis Asymmetry Catalysis Catalysts Chemical Sciences Cheminformatics Chemistry chiral rhodium catalyst cyclopropane diazo derivatives fluorine Medicinal Chemistry Methodology or physical chemistry Organic chemistry Rhodium Synthesis Theoretical and |
| title | Catalytic Enantioselective Synthesis of Halocyclopropanes |
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