Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers
Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imi...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2009-04, Vol.2009 (10), p.1606-1611 |
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| container_issue | 10 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2009 |
| creator | Abecassis, Keren Gibson, Susan E. Martin‐Fontecha, Mar |
| description | Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imidazole alcohols, a triol and a tertiary alcohol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group. |
| doi_str_mv | 10.1002/ejoc.200900007 |
| format | Article |
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The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200900007</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag</publisher><subject>Alcohols ; Alkylation ; Allylic compounds ; Chemistry ; Chiral base ; Chromium ; Coordination compounds ; Enantioselectivity ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Inorganic chemistry and origins of life ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties</subject><ispartof>European Journal of Organic Chemistry, 2009-04, Vol.2009 (10), p.1606-1611</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3197-95628081b1acc7d6b1e30b83ffac5616e9cba07e2ed660c2d7b1278d5aa8a0c23</citedby><cites>FETCH-LOGICAL-c3197-95628081b1acc7d6b1e30b83ffac5616e9cba07e2ed660c2d7b1278d5aa8a0c23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.200900007$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200900007$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,780,784,792,1417,27921,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21244157$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Abecassis, Keren</creatorcontrib><creatorcontrib>Gibson, Susan E.</creatorcontrib><creatorcontrib>Martin‐Fontecha, Mar</creatorcontrib><title>Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers</title><title>European Journal of Organic Chemistry</title><description>Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imidazole alcohols, a triol and a tertiary alcohol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group.</description><subject>Alcohols</subject><subject>Alkylation</subject><subject>Allylic compounds</subject><subject>Chemistry</subject><subject>Chiral base</subject><subject>Chromium</subject><subject>Coordination compounds</subject><subject>Enantioselectivity</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Inorganic chemistry and origins of life</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFUE1LwzAYDqLgnF495yLooTNJ27Q5zlK_GOywCd5KmqY0I01GMnX115s60aPv4f2A54P3AeASoxlGiNzKjRUzghBDobIjMMGIsQhRho7DnsRJhFn8egrOvN8EBKMUT8B-NZhdJ73y0LawNNzslJXGKdHJBq6ksKbhboDcNHAt3U6Nx1wL21nt4bvicB2w3NXWDFp0zvbqrb9GN7Cw_VbLvfzWvZPmc9CBp0Mvg5_z5-Ck5drLi585BS_35bp4jBbLh6divohEjFkWsZSSHOW4xlyIrKE1ljGq87htuUgpppKJmqNMEtlQigRpshqTLG9SznMe7ngKZgdd4az3TrbV1qk-fFFhVI25VWNu1W9ugXB1IGy5F1y3jhuh_C-LYJIkOB1x7ID7UFoO_6hW5fOy-PP4ApWUgVk</recordid><startdate>200904</startdate><enddate>200904</enddate><creator>Abecassis, Keren</creator><creator>Gibson, Susan E.</creator><creator>Martin‐Fontecha, Mar</creator><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200904</creationdate><title>Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers</title><author>Abecassis, Keren ; Gibson, Susan E. ; Martin‐Fontecha, Mar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3197-95628081b1acc7d6b1e30b83ffac5616e9cba07e2ed660c2d7b1278d5aa8a0c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alcohols</topic><topic>Alkylation</topic><topic>Allylic compounds</topic><topic>Chemistry</topic><topic>Chiral base</topic><topic>Chromium</topic><topic>Coordination compounds</topic><topic>Enantioselectivity</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Inorganic chemistry and origins of life</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abecassis, Keren</creatorcontrib><creatorcontrib>Gibson, Susan E.</creatorcontrib><creatorcontrib>Martin‐Fontecha, Mar</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abecassis, Keren</au><au>Gibson, Susan E.</au><au>Martin‐Fontecha, Mar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers</atitle><jtitle>European Journal of Organic Chemistry</jtitle><date>2009-04</date><risdate>2009</risdate><volume>2009</volume><issue>10</issue><spage>1606</spage><epage>1611</epage><pages>1606-1611</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imidazole alcohols, a triol and a tertiary alcohol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag</pub><doi>10.1002/ejoc.200900007</doi><tpages>6</tpages></addata></record> |
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| ispartof | European Journal of Organic Chemistry, 2009-04, Vol.2009 (10), p.1606-1611 |
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| source | Wiley Online Library All Journals |
| subjects | Alcohols Alkylation Allylic compounds Chemistry Chiral base Chromium Coordination compounds Enantioselectivity Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Inorganic chemistry and origins of life Noncondensed benzenic compounds Organic chemistry Preparations and properties |
| title | Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers |
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