Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst
A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole‐derived organocatalyst. Computational and NMR studies sup...
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| Veröffentlicht in: | European journal of organic chemistry 2013-03, Vol.2013 (8), p.1434-1440 |
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| container_title | European journal of organic chemistry |
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| creator | Gómez-Torres, Eduardo Alonso, Diego A. Gómez-Bengoa, Enrique Nájera, Carmen |
| description | A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole‐derived organocatalyst. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process.
The chiral 2‐aminobenzimidazole‐derived catalyst 5f serves as very efficient and selective bifunctional organocatalyst in the asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimide and N‐substituted maleimides. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process. |
| doi_str_mv | 10.1002/ejoc.201201046 |
| format | Article |
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The chiral 2‐aminobenzimidazole‐derived catalyst 5f serves as very efficient and selective bifunctional organocatalyst in the asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimide and N‐substituted maleimides. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201201046</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Asymmetric catalysis ; Hydrogen bonds ; Michael addition ; Organocatalysis ; Transition states</subject><ispartof>European journal of organic chemistry, 2013-03, Vol.2013 (8), p.1434-1440</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-c4616-18958d5820fb51dbd19bc00cdcd026f5bd9c06af3a6308241ab79ebba74405d03</citedby><cites>FETCH-LOGICAL-c4616-18958d5820fb51dbd19bc00cdcd026f5bd9c06af3a6308241ab79ebba74405d03</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.201201046$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201201046$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Gómez-Torres, Eduardo</creatorcontrib><creatorcontrib>Alonso, Diego A.</creatorcontrib><creatorcontrib>Gómez-Bengoa, Enrique</creatorcontrib><creatorcontrib>Nájera, Carmen</creatorcontrib><title>Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole‐derived organocatalyst. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process.
The chiral 2‐aminobenzimidazole‐derived catalyst 5f serves as very efficient and selective bifunctional organocatalyst in the asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimide and N‐substituted maleimides. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process.</description><subject>Asymmetric catalysis</subject><subject>Hydrogen bonds</subject><subject>Michael addition</subject><subject>Organocatalysis</subject><subject>Transition states</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkU1v1DAQhiMEEqVw5WyJC0hkGceOEx9L2BZQy0oUVG6Wv8J68dqLnQWyf4i_ScJWFTekkWYOz_PO4S2KpxgWGKB6ZTdRLyrA0wBl94oTDJyXwDjcn25KaIk5-fKweJTzBgA4Y_ik-L0MMgwuZuutHtwPi67HMKxtdhnFHl3vtXbBbZ2xGakRXTm9ltajM2PcZIWZwS9J-cZpmVQMo0dd3O7iPpiMhoiupLe3dicH6ceDNXOORN3aJenRa5efV6XcuhCVDYeZlYfo7Qu0Sl9liPqvlYfHxYNe-myf3O7T4vP58lP3trxcXbzrzi5LTRlmJW553Zq6raBXNTbKYK40gDbaQMX6WhmugcmeSEagrSiWquFWKdlQCrUBclo8O-buUvy-t3kQm7hPYXopMMEN5TVr8EQtjpROMedke7FLbivTKDCIuQwxlyHuypgEfhR-Om_H_9Bi-X7V_euWR9flwf66c2X6JlhDmlrcfLgQN1XX4vOPRFDyB1Oan8E</recordid><startdate>201303</startdate><enddate>201303</enddate><creator>Gómez-Torres, Eduardo</creator><creator>Alonso, Diego A.</creator><creator>Gómez-Bengoa, Enrique</creator><creator>Nájera, Carmen</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>201303</creationdate><title>Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst</title><author>Gómez-Torres, Eduardo ; Alonso, Diego A. ; Gómez-Bengoa, Enrique ; Nájera, Carmen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4616-18958d5820fb51dbd19bc00cdcd026f5bd9c06af3a6308241ab79ebba74405d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Asymmetric catalysis</topic><topic>Hydrogen bonds</topic><topic>Michael addition</topic><topic>Organocatalysis</topic><topic>Transition states</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gómez-Torres, Eduardo</creatorcontrib><creatorcontrib>Alonso, Diego A.</creatorcontrib><creatorcontrib>Gómez-Bengoa, Enrique</creatorcontrib><creatorcontrib>Nájera, Carmen</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>Gómez-Torres, Eduardo</au><au>Alonso, Diego A.</au><au>Gómez-Bengoa, Enrique</au><au>Nájera, Carmen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2013-03</date><risdate>2013</risdate><volume>2013</volume><issue>8</issue><spage>1434</spage><epage>1440</epage><pages>1434-1440</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole‐derived organocatalyst. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process.
The chiral 2‐aminobenzimidazole‐derived catalyst 5f serves as very efficient and selective bifunctional organocatalyst in the asymmetric conjugate addition of 1,3‐dicarbonyl compounds to maleimide and N‐substituted maleimides. Computational and NMR studies support the hydrogen‐bonding activation role of the catalyst and the origin of the stereoselectivity of the process.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201201046</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Asymmetric catalysis Hydrogen bonds Michael addition Organocatalysis Transition states |
| title | Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst |
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