Efficient Pseudo-enantiomeric Carbohydrate Olefin Ligands
Highly efficient pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral sub...
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| Veröffentlicht in: | Organic letters 2012-07, Vol.14 (14), p.3780-3783 |
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| container_title | Organic letters |
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| creator | Grugel, Holger Albrecht, Fabian Minuth, Tobias Boysen, Mike M. K |
| description | Highly efficient pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral substrates. Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic resolution steps, making them a valuable addition to the arsenal of chiral ligands with olefinic donor sites. |
| doi_str_mv | 10.1021/ol3015896 |
| format | Article |
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Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic resolution steps, making them a valuable addition to the arsenal of chiral ligands with olefinic donor sites.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol3015896</identifier><identifier>PMID: 22780685</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemistry ; Carbohydrates - chemistry ; Catalysis ; Galactose - chemistry ; Glucose - chemistry ; Ligands ; Molecular Structure ; Stereoisomerism</subject><ispartof>Organic letters, 2012-07, Vol.14 (14), p.3780-3783</ispartof><rights>Copyright © 2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-347ad5f1a776ed8b79bb3bc3bddca9b4b4c18af1f2552285d52fc61c471bf1783</citedby><cites>FETCH-LOGICAL-a315t-347ad5f1a776ed8b79bb3bc3bddca9b4b4c18af1f2552285d52fc61c471bf1783</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/ol3015896$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol3015896$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22780685$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Grugel, Holger</creatorcontrib><creatorcontrib>Albrecht, Fabian</creatorcontrib><creatorcontrib>Minuth, Tobias</creatorcontrib><creatorcontrib>Boysen, Mike M. 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Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic resolution steps, making them a valuable addition to the arsenal of chiral ligands with olefinic donor sites.</description><subject>Alkenes - chemistry</subject><subject>Carbohydrates - chemistry</subject><subject>Catalysis</subject><subject>Galactose - chemistry</subject><subject>Glucose - chemistry</subject><subject>Ligands</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkD1PwzAQhi0EoqUw8AdQFiQYAj47jpMRVeVDqlQGmCN_gqvELnYy9N83qKUT051Oz_tK9yB0DfgBMIHH0FIMrKrLEzQFRmjOMSOnx73EE3SR0hpjGC_1OZoQwitcVmyK6oW1Tjnj--w9mUGH3Hjhexc6E53K5iLK8L3VUfQmW7XGOp8t3ZfwOl2iMyvaZK4Oc4Y-nxcf89d8uXp5mz8tc0GB9TktuNDMguC8NLqSvJaSSkWl1krUspCFgkpYsIQxQiqmGbGqBFVwkBZ4RWfobt-7ieFnMKlvOpeUaVvhTRhSA0VdwxjkbETv96iKIaVobLOJrhNx2wBufk01R1Mje3OoHWRn9JH8UzMCt3tAqNSswxD9-OU_RTvppm7B</recordid><startdate>20120720</startdate><enddate>20120720</enddate><creator>Grugel, Holger</creator><creator>Albrecht, Fabian</creator><creator>Minuth, Tobias</creator><creator>Boysen, Mike M. 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Lett</addtitle><date>2012-07-20</date><risdate>2012</risdate><volume>14</volume><issue>14</issue><spage>3780</spage><epage>3783</epage><pages>3780-3783</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Highly efficient pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral substrates. Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic resolution steps, making them a valuable addition to the arsenal of chiral ligands with olefinic donor sites.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22780685</pmid><doi>10.1021/ol3015896</doi><tpages>4</tpages></addata></record> |
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| ispartof | Organic letters, 2012-07, Vol.14 (14), p.3780-3783 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Alkenes - chemistry Carbohydrates - chemistry Catalysis Galactose - chemistry Glucose - chemistry Ligands Molecular Structure Stereoisomerism |
| title | Efficient Pseudo-enantiomeric Carbohydrate Olefin Ligands |
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