Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation
Several new classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. Oxazole, thiazole, and imidazole-based chiral precatalysts were prepared in several steps from amino a...
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| Veröffentlicht in: | Tetrahedron 2016-07, Vol.72 (27-28), p.3905-3916 |
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| container_issue | 27-28 |
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| container_title | Tetrahedron |
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| creator | Wiedenhoeft, Dennis Benoit, Adam R. Wu, Yibiao Porter, Jacob D. Meyle, Elisia Yeung, Teresa H.W. Huff, Raechel Lindeman, Sergey V. Dockendorff, Chris |
| description | Several new classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. Oxazole, thiazole, and imidazole-based chiral precatalysts were prepared in several steps from amino acid starting materials, and these were combined with a variety of metal Lewis acids for potential use as catalysts for various carbon–carbon bond formations. Air- and moisture-tolerant catalysts for enantioselective direct aldol reactions with activated benzaldehyde acceptors were identified, with optimal results obtained with proline-derived oxazole–carboxamide precatalysts combined with Zn(OTf)2 or lanthanide (III) salts. Control studies support the hypothesis that these act as unimolecular hybrid catalysts for the aldol reaction of propionaldehyde and 4-nitrobenzaldehyde.
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| doi_str_mv | 10.1016/j.tet.2016.05.014 |
| format | Article |
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[Display omitted]</description><subject>Aldehydes</subject><subject>Aldol reaction</subject><subject>Benzaldehyde</subject><subject>Bonding</subject><subject>Carbon-carbon composites</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Heterocycle</subject><subject>Hybrid catalyst</subject><subject>Lewis acid</subject><subject>Organocatalyst</subject><subject>Scaffolds</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9UMtOwzAQtBBIlMIHcMuRS9LdxHETcUKIl1TEBc6W44fqKo2L7YJ64x_4Q74ER-HMSqudkXZmtUPIJUKBgGyxKaKORZlgAXUBSI_IDCmjeU2RHZMZAIWcQgmn5CyEDQAgltWMhOd9H63ZDzJaN4g-W-uovZMH2VuZBSmMcb0KmXE-Wx86b1W20p82ZEJatZhgJ4LOpIiiP4REnUnEd274-fqeQJZajRZbMV45JydG9EFf_M05ebu_e719zFcvD0-3N6tc0qqNeQ3KABOCQo2dkKZdqpZRyiqUBlvABuuqaZb1smK66pqKAjNKGIQWGrksu2pOribfnXfvex0i39ogdd-LQbt94NiU9VisTKs4rUrvQvDa8J23W-EPHIGPAfMNTwHzMWAONU8BJ831pNHphw-rPQ_S6kFqZb2WkStn_1H_AhaZhbg</recordid><startdate>20160707</startdate><enddate>20160707</enddate><creator>Wiedenhoeft, Dennis</creator><creator>Benoit, Adam R.</creator><creator>Wu, Yibiao</creator><creator>Porter, Jacob D.</creator><creator>Meyle, Elisia</creator><creator>Yeung, Teresa H.W.</creator><creator>Huff, Raechel</creator><creator>Lindeman, Sergey V.</creator><creator>Dockendorff, Chris</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160707</creationdate><title>Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation</title><author>Wiedenhoeft, Dennis ; Benoit, Adam R. ; Wu, Yibiao ; Porter, Jacob D. ; Meyle, Elisia ; Yeung, Teresa H.W. ; Huff, Raechel ; Lindeman, Sergey V. ; Dockendorff, Chris</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-50df06aa4051bacf97d9644631cf190181538875736e3b83406fdaf10908c72b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Aldehydes</topic><topic>Aldol reaction</topic><topic>Benzaldehyde</topic><topic>Bonding</topic><topic>Carbon-carbon composites</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Heterocycle</topic><topic>Hybrid catalyst</topic><topic>Lewis acid</topic><topic>Organocatalyst</topic><topic>Scaffolds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wiedenhoeft, Dennis</creatorcontrib><creatorcontrib>Benoit, Adam R.</creatorcontrib><creatorcontrib>Wu, Yibiao</creatorcontrib><creatorcontrib>Porter, Jacob D.</creatorcontrib><creatorcontrib>Meyle, Elisia</creatorcontrib><creatorcontrib>Yeung, Teresa H.W.</creatorcontrib><creatorcontrib>Huff, Raechel</creatorcontrib><creatorcontrib>Lindeman, Sergey V.</creatorcontrib><creatorcontrib>Dockendorff, Chris</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wiedenhoeft, Dennis</au><au>Benoit, Adam R.</au><au>Wu, Yibiao</au><au>Porter, Jacob D.</au><au>Meyle, Elisia</au><au>Yeung, Teresa H.W.</au><au>Huff, Raechel</au><au>Lindeman, Sergey V.</au><au>Dockendorff, Chris</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation</atitle><jtitle>Tetrahedron</jtitle><date>2016-07-07</date><risdate>2016</risdate><volume>72</volume><issue>27-28</issue><spage>3905</spage><epage>3916</epage><pages>3905-3916</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Several new classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. 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| ispartof | Tetrahedron, 2016-07, Vol.72 (27-28), p.3905-3916 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Aldehydes Aldol reaction Benzaldehyde Bonding Carbon-carbon composites Catalysis Catalysts Heterocycle Hybrid catalyst Lewis acid Organocatalyst Scaffolds |
| title | Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation |
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