Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates
The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam...
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| Veröffentlicht in: | Journal of organic chemistry 2011-03, Vol.76 (6), p.1945-1948 |
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| container_end_page | 1948 |
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| container_issue | 6 |
| container_start_page | 1945 |
| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | López-Pérez, Ana Segler, Marwin Adrio, Javier Carretero, Juan C |
| description | The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields. |
| doi_str_mv | 10.1021/jo1024915 |
| format | Article |
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The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo1024915</identifier><identifier>PMID: 21332240</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acrylates - chemistry ; Azo Compounds - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Silver - chemistry ; Stereoisomerism ; Substrate Specificity ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields.</description><subject>Acrylates - chemistry</subject><subject>Azo Compounds - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</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><subject>Silver - chemistry</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Thiosemicarbazones - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtKAzEUBuAgitbLwheQ2YgIjuY2mc6y1isILlTE1XBMztBIOqnJVGkfywfxmYxY7cazOGfz8R_4Cdll9JhRzk5efDqyYsUK6bGC01xVVK6SHqWc54IrsUE2Y3yhaYqiWCcbnAnBuaQ98nhn3RuGfAgduNkcTcaORH5mJ95ByIYz7TwYYzvr28w32WDux9iNbIvZk7MGY_Zuu1H2-ZGf-jBz2UCnDR3GbbLWgIu4s7hb5OHi_H54ld_cXl4PBzc5CCm73KBSfVE0DLQoqdIKFRaCS4CS6kpXytCyj5oZgyVIzgXyymiTaF9VukGxRQ5-cifBv04xdvXYRo3OQYt-Guu-EpKXUrIkD3-kDj7GgE09CXYMYVYzWn_XWP_VmOzeInX6PEbzJ397S2B_ASBqcE2AVtu4dKKSUlC5dKBjyp-GNpXxz8Mvyy-FlQ</recordid><startdate>20110318</startdate><enddate>20110318</enddate><creator>López-Pérez, Ana</creator><creator>Segler, Marwin</creator><creator>Adrio, Javier</creator><creator>Carretero, Juan C</creator><general>American Chemical Society</general><scope>IQODW</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></search><sort><creationdate>20110318</creationdate><title>Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates</title><author>López-Pérez, Ana ; Segler, Marwin ; Adrio, Javier ; Carretero, Juan C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-de66835f1ac3706c6e6e5324aa70c9c96d078ec1dde7a4223e29dcd706869cfe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Acrylates - chemistry</topic><topic>Azo Compounds - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</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><topic>Silver - chemistry</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Thiosemicarbazones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>López-Pérez, Ana</creatorcontrib><creatorcontrib>Segler, Marwin</creatorcontrib><creatorcontrib>Adrio, Javier</creatorcontrib><creatorcontrib>Carretero, Juan C</creatorcontrib><collection>Pascal-Francis</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><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>López-Pérez, Ana</au><au>Segler, Marwin</au><au>Adrio, Javier</au><au>Carretero, Juan C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-03-18</date><risdate>2011</risdate><volume>76</volume><issue>6</issue><spage>1945</spage><epage>1948</epage><pages>1945-1948</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21332240</pmid><doi>10.1021/jo1024915</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Acrylates - chemistry Azo Compounds - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Silver - chemistry Stereoisomerism Substrate Specificity Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Thiosemicarbazones - chemistry |
| title | Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates |
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