Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction
The asymmetric domino reaction of various α,α‐dicyano olefins to 3‐nitro‐2H‐chromenes was studied employing readily available cinchona‐derived bifunctional thioureas as organocatalysts. These new transformations were highly regio‐, chemo‐, diastereo‐, and enantioselective simultaneously giving chira...
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| Veröffentlicht in: | European journal of organic chemistry 2012-12, Vol.2012 (35), p.6924-6932 |
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| container_issue | 35 |
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| container_title | European journal of organic chemistry |
| container_volume | 2012 |
| creator | Guo, Zhi-Wei Li, Xin-Sheng Zhu, Wei-Dong Xie, Jian-Wu |
| description | The asymmetric domino reaction of various α,α‐dicyano olefins to 3‐nitro‐2H‐chromenes was studied employing readily available cinchona‐derived bifunctional thioureas as organocatalysts. These new transformations were highly regio‐, chemo‐, diastereo‐, and enantioselective simultaneously giving chiral multi‐functionalized polyheterocyclic benzopyran derivatives with multi‐chiral carbon centers.
Chiral multi‐functionalized polyheterocyclic benzopyran derivatives were easily obtained with excellent diastereoselectivities and good‐to‐excellent enantioselectivities from electron‐deficient α,α‐dicyano olefins and 3‐nitro‐2H‐chromene derivatives under mild and simple conditions. |
| doi_str_mv | 10.1002/ejoc.201200928 |
| format | Article |
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Chiral multi‐functionalized polyheterocyclic benzopyran derivatives were easily obtained with excellent diastereoselectivities and good‐to‐excellent enantioselectivities from electron‐deficient α,α‐dicyano olefins and 3‐nitro‐2H‐chromene derivatives under mild and simple conditions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201200928</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Asymmetric synthesis ; Biological and medical sciences ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Diastereoselectivity ; Domino reactions ; Exact sciences and technology ; General and physical chemistry ; General pharmacology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Medical sciences ; Organic chemistry ; Organocatalysis ; Oxygen heterocycles ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Preparations and properties ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>European journal of organic chemistry, 2012-12, Vol.2012 (35), p.6924-6932</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 INIST-CNRS</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4518-11cb9735278927c3c142f3b9052f54534247fc6a643e3b3f75279bb30001050a3</citedby><cites>FETCH-LOGICAL-c4518-11cb9735278927c3c142f3b9052f54534247fc6a643e3b3f75279bb30001050a3</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.201200928$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201200928$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27029746$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Zhi-Wei</creatorcontrib><creatorcontrib>Li, Xin-Sheng</creatorcontrib><creatorcontrib>Zhu, Wei-Dong</creatorcontrib><creatorcontrib>Xie, Jian-Wu</creatorcontrib><title>Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The asymmetric domino reaction of various α,α‐dicyano olefins to 3‐nitro‐2H‐chromenes was studied employing readily available cinchona‐derived bifunctional thioureas as organocatalysts. These new transformations were highly regio‐, chemo‐, diastereo‐, and enantioselective simultaneously giving chiral multi‐functionalized polyheterocyclic benzopyran derivatives with multi‐chiral carbon centers.
Chiral multi‐functionalized polyheterocyclic benzopyran derivatives were easily obtained with excellent diastereoselectivities and good‐to‐excellent enantioselectivities from electron‐deficient α,α‐dicyano olefins and 3‐nitro‐2H‐chromene derivatives under mild and simple conditions.</description><subject>Asymmetric synthesis</subject><subject>Biological and medical sciences</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Diastereoselectivity</subject><subject>Domino reactions</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>General pharmacology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Medical sciences</subject><subject>Organic chemistry</subject><subject>Organocatalysis</subject><subject>Oxygen heterocycles</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Preparations and properties</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOHDEQRVsRkQIk26wtIZY98dvjJTSPgAiDSBBRNpbbcYMHT3uw3ZDmE_LVMQwascuqXOVzb6luVX1GcIIgxF_sPJgJhghDKPH0XbWJoJQ15BJulDcltEaS_PxQbaU0h4XhHG1Wf5vQpxwHk13oQehAc-ui9uDb4LOrj4b-5UN792R_g4vgx1ubbQxmNN4ZsG_7p7Aco-7BgY3uQWf3YBNoR3CVXH8DynwvjYuFzbHQs3ij-2B01n7MpT8IC9cHcGn1y5KP1ftO-2Q_vdbt6uro8EfztT6bHZ80e2e1oQxNa4RMKwVhWEwlFoYYRHFHWgkZ7hhlhGIqOsM1p8SSlnSikLJtSTkZQQY12a52Vr7LGO4Hm7KahyGWG5NCgvMp4pjBQk1WlIkhpWg7tYxuoeOoEFTPeavnvNU67yLYfbXVyWjflVCMS2sVFhBLQXnh5Ip7dN6O_3FVh6ez5u2OeqV1Kds_a62Od4oLIpi6Pj9W5Be9vP7OTtUF-QfaYKJB</recordid><startdate>201212</startdate><enddate>201212</enddate><creator>Guo, Zhi-Wei</creator><creator>Li, Xin-Sheng</creator><creator>Zhu, Wei-Dong</creator><creator>Xie, Jian-Wu</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201212</creationdate><title>Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction</title><author>Guo, Zhi-Wei ; Li, Xin-Sheng ; Zhu, Wei-Dong ; Xie, Jian-Wu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4518-11cb9735278927c3c142f3b9052f54534247fc6a643e3b3f75279bb30001050a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Asymmetric synthesis</topic><topic>Biological and medical sciences</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Diastereoselectivity</topic><topic>Domino reactions</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>General pharmacology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Medical sciences</topic><topic>Organic chemistry</topic><topic>Organocatalysis</topic><topic>Oxygen heterocycles</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Preparations and properties</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Zhi-Wei</creatorcontrib><creatorcontrib>Li, Xin-Sheng</creatorcontrib><creatorcontrib>Zhu, Wei-Dong</creatorcontrib><creatorcontrib>Xie, Jian-Wu</creatorcontrib><collection>Istex</collection><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>Guo, Zhi-Wei</au><au>Li, Xin-Sheng</au><au>Zhu, Wei-Dong</au><au>Xie, Jian-Wu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2012-12</date><risdate>2012</risdate><volume>2012</volume><issue>35</issue><spage>6924</spage><epage>6932</epage><pages>6924-6932</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The asymmetric domino reaction of various α,α‐dicyano olefins to 3‐nitro‐2H‐chromenes was studied employing readily available cinchona‐derived bifunctional thioureas as organocatalysts. These new transformations were highly regio‐, chemo‐, diastereo‐, and enantioselective simultaneously giving chiral multi‐functionalized polyheterocyclic benzopyran derivatives with multi‐chiral carbon centers.
Chiral multi‐functionalized polyheterocyclic benzopyran derivatives were easily obtained with excellent diastereoselectivities and good‐to‐excellent enantioselectivities from electron‐deficient α,α‐dicyano olefins and 3‐nitro‐2H‐chromene derivatives under mild and simple conditions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201200928</doi><tpages>9</tpages></addata></record> |
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| subjects | Asymmetric synthesis Biological and medical sciences Catalysis Catalysts: preparations and properties Chemistry Diastereoselectivity Domino reactions Exact sciences and technology General and physical chemistry General pharmacology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Medical sciences Organic chemistry Organocatalysis Oxygen heterocycles Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction |
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