Regio- and Diastereoselective Crotylboration of vic-Tricarbonyl Compounds
Crotylboration of vic‐diketoamides and vic‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti), Lewis acid prom...
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| Veröffentlicht in: | European journal of organic chemistry 2013-02, Vol.2013 (4), p.662-665 |
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| container_title | European journal of organic chemistry |
| container_volume | 2013 |
| creator | Roßbach, Jan Baumeister, Julia Harms, Klaus Koert, Ulrich |
| description | Crotylboration of vic‐diketoamides and vic‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti), Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.
(E)‐Crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti). Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer. |
| doi_str_mv | 10.1002/ejoc.201201517 |
| format | Article |
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(E)‐Crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti). Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201201517</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Beta ; Crotylboration ; Diastereoselectivity ; Regioselectivity ; Synthetic methods ; vic-Tricarbonyl compounds</subject><ispartof>European journal of organic chemistry, 2013-02, Vol.2013 (4), p.662-665</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3957-f675137b2ac77dfbd1021cce712c6fc9326aecc46b6dcd67014ec3a83da94aa73</citedby><cites>FETCH-LOGICAL-c3957-f675137b2ac77dfbd1021cce712c6fc9326aecc46b6dcd67014ec3a83da94aa73</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.201201517$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201201517$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids></links><search><creatorcontrib>Roßbach, Jan</creatorcontrib><creatorcontrib>Baumeister, Julia</creatorcontrib><creatorcontrib>Harms, Klaus</creatorcontrib><creatorcontrib>Koert, Ulrich</creatorcontrib><title>Regio- and Diastereoselective Crotylboration of vic-Tricarbonyl Compounds</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Crotylboration of vic‐diketoamides and vic‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti), Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.
(E)‐Crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti). Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.</description><subject>Beta</subject><subject>Crotylboration</subject><subject>Diastereoselectivity</subject><subject>Regioselectivity</subject><subject>Synthetic methods</subject><subject>vic-Tricarbonyl compounds</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAYhoMoOKdXzwXPmfnRJstR6pyT6VAnipeQpqlkds2WdNP-93ZUhjfhg_c7vM_3wQPAOUYDjBC5NAunBwThdhLMD0APIyEgYgIdtntMY4gFfTsGJyEsEEKCMdwDkyfzYR2MVJVH11aF2njjgimNru3WRKl3dVNmzqvauipyRbS1Gs691cpnrmrKKHXLldtUeTgFR4Uqgzn7zT54uRnN01s4nY0n6dUUaioSDgvGE0x5RpTmPC-yHCOCtTYcE80KLShhymgds4zlOmcc4dhoqoY0VyJWitM-uOjurrxbb0yo5cJtfNW-lJhwghIxTEjbGnQt7V0I3hRy5e1S-UZiJHe65E6X3OtqAdEBX7Y0zT9tObqbpX9Z2LG29fe9Z5X_lIxTnsjXh7F85ozcvz8OJaU_Zj5-pg</recordid><startdate>201302</startdate><enddate>201302</enddate><creator>Roßbach, Jan</creator><creator>Baumeister, Julia</creator><creator>Harms, Klaus</creator><creator>Koert, Ulrich</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201302</creationdate><title>Regio- and Diastereoselective Crotylboration of vic-Tricarbonyl Compounds</title><author>Roßbach, Jan ; Baumeister, Julia ; Harms, Klaus ; Koert, Ulrich</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3957-f675137b2ac77dfbd1021cce712c6fc9326aecc46b6dcd67014ec3a83da94aa73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Beta</topic><topic>Crotylboration</topic><topic>Diastereoselectivity</topic><topic>Regioselectivity</topic><topic>Synthetic methods</topic><topic>vic-Tricarbonyl compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Roßbach, Jan</creatorcontrib><creatorcontrib>Baumeister, Julia</creatorcontrib><creatorcontrib>Harms, Klaus</creatorcontrib><creatorcontrib>Koert, Ulrich</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Roßbach, Jan</au><au>Baumeister, Julia</au><au>Harms, Klaus</au><au>Koert, Ulrich</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio- and Diastereoselective Crotylboration of vic-Tricarbonyl Compounds</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2013-02</date><risdate>2013</risdate><volume>2013</volume><issue>4</issue><spage>662</spage><epage>665</epage><pages>662-665</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Crotylboration of vic‐diketoamides and vic‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti), Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.
(E)‐Crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti). Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201201517</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Beta Crotylboration Diastereoselectivity Regioselectivity Synthetic methods vic-Tricarbonyl compounds |
| title | Regio- and Diastereoselective Crotylboration of vic-Tricarbonyl Compounds |
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