Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes
The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of 98:98:
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Veröffentlicht in: | Journal of the American Chemical Society 2009-03, Vol.131 (11), p.3844-3845 |
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container_title | Journal of the American Chemical Society |
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creator | Ibrahem, Ismail Yu, Miao Schrock, Richard R Hoveyda, Amir H |
description | The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of 98:98: |
doi_str_mv | 10.1021/ja900097n |
format | Article |
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Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50−85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (≥87:13 Z/E).</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja900097n</identifier><identifier>PMID: 19249833</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes ; Catalysis ; Cyclization ; Molybdenum ; Organometallic Compounds ; Pyrans - chemical synthesis ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2009-03, Vol.131 (11), p.3844-3845</ispartof><rights>Copyright © 2009 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a469t-33aab198b1210873c1ea34ddc5db7c7420166d1760596eb1d86ee8ae80a49c143</citedby><cites>FETCH-LOGICAL-a469t-33aab198b1210873c1ea34ddc5db7c7420166d1760596eb1d86ee8ae80a49c143</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/ja900097n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja900097n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19249833$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ibrahem, Ismail</creatorcontrib><creatorcontrib>Yu, Miao</creatorcontrib><creatorcontrib>Schrock, Richard R</creatorcontrib><creatorcontrib>Hoveyda, Amir H</creatorcontrib><title>Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50−85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (≥87:13 Z/E).</description><subject>Alkenes</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Molybdenum</subject><subject>Organometallic Compounds</subject><subject>Pyrans - chemical synthesis</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkUFrFDEUx4NY7LZ68AtILgo9pE0yM5mZi1CGaoWWQtWLl_Amed3NMpOsk2xxPPjZTdmlteDpkeSX33u8PyFvBT8VXIqzNbSc87b2L8hCVJKzSkj1kizypWR1o4pDchTjOh9L2YhX5FC0smyboliQP5duuRpm-oNR8JZeePDJhYgDmuTukd46v2Q3G_S5nnVTiJFdY4K0wugivUXIWPCRdpBgmH-jpf1MvyacMCzzJ8MgsetAzy2M2TwPbnQ20C6MmwF_YXxNDu5giPhmX4_J908X37pLdnXz-Ut3fsWgVG1iRQHQi7bphRS8qQsjEIrSWlPZvjZ1KblQyopa8apV2AvbKMQGsOFQtkaUxTH5uPNutv2I1qBPEwx6M7kRplkHcPr5i3crvQz3WqpGyLLKgg97wRR-bjEmPbpocBjAY9hGrWpeqtw8gyc70Dwsa8K7xyaC64e09GNamX3371RP5D6eDLzfAWCiXoft5POS_iP6C69Onqk</recordid><startdate>20090325</startdate><enddate>20090325</enddate><creator>Ibrahem, Ismail</creator><creator>Yu, Miao</creator><creator>Schrock, Richard R</creator><creator>Hoveyda, Amir H</creator><general>American Chemical Society</general><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>5PM</scope></search><sort><creationdate>20090325</creationdate><title>Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes</title><author>Ibrahem, Ismail ; Yu, Miao ; Schrock, Richard R ; Hoveyda, Amir H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a469t-33aab198b1210873c1ea34ddc5db7c7420166d1760596eb1d86ee8ae80a49c143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkenes</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Molybdenum</topic><topic>Organometallic Compounds</topic><topic>Pyrans - chemical synthesis</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ibrahem, Ismail</creatorcontrib><creatorcontrib>Yu, Miao</creatorcontrib><creatorcontrib>Schrock, Richard R</creatorcontrib><creatorcontrib>Hoveyda, Amir H</creatorcontrib><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>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ibrahem, Ismail</au><au>Yu, Miao</au><au>Schrock, Richard R</au><au>Hoveyda, Amir H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2009-03-25</date><risdate>2009</risdate><volume>131</volume><issue>11</issue><spage>3844</spage><epage>3845</epage><pages>3844-3845</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50−85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (≥87:13 Z/E).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19249833</pmid><doi>10.1021/ja900097n</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Alkenes Catalysis Cyclization Molybdenum Organometallic Compounds Pyrans - chemical synthesis Stereoisomerism |
title | Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes |
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