Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis
A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester interme...
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| Veröffentlicht in: | Organic letters 2013-01, Vol.15 (1), p.50-53 |
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| container_end_page | 53 |
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| container_title | Organic letters |
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| creator | Mo, Junming Yang, Ruojie Chen, Xingkuan Tiwari, Bhoopendra Chi, Yonggui Robin |
| description | A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones. |
| doi_str_mv | 10.1021/ol303035r |
| format | Article |
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The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol303035r</identifier><identifier>PMID: 23249417</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Catalysis ; Heterocyclic Compounds - chemistry ; Ketones - chemistry ; Methane - analogs & derivatives ; Methane - chemistry ; Molecular Structure ; Oxidation-Reduction</subject><ispartof>Organic letters, 2013-01, Vol.15 (1), p.50-53</ispartof><rights>Copyright © 2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-f448b3186ba7d83e423a5afefe38a1f60c847d298a82c6e452b74aec5b2aef83</citedby><cites>FETCH-LOGICAL-a315t-f448b3186ba7d83e423a5afefe38a1f60c847d298a82c6e452b74aec5b2aef83</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/ol303035r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol303035r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27078,27926,27927,56740,56790</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23249417$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mo, Junming</creatorcontrib><creatorcontrib>Yang, Ruojie</creatorcontrib><creatorcontrib>Chen, Xingkuan</creatorcontrib><creatorcontrib>Tiwari, Bhoopendra</creatorcontrib><creatorcontrib>Chi, Yonggui Robin</creatorcontrib><title>Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.</description><subject>Aldehydes - chemistry</subject><subject>Catalysis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Ketones - chemistry</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkD1Ow0AQRlcIREKg4ALIDRIUhv1z7JRRIAQpIgXprfF6LDZax2HXjjAVV-AoXIRDcBI2SkiFpvhGozdf8Qg5Z_SGUc5uKyOon8gekC6LuAhjGvHD_d6nHXLi3IJS5i-DY9LhgsuBZHGXZHfaoqqD76-fj89xs1S1rpZg9DtslqAqgmddrgwGQ5PjS5ujC9Yagtmbzj2xxuDJ_02wRlupVhmtghHYDJfoswbTOu1OyVEBxuHZLntkPr6fjybhdPbwOBpOQxAsqsNCyiQTLOlnEOeJQMkFRFBggSIBVvSpSmSc80ECCVd9lBHPYgmooowDFonokatt7cpWrw26Oi21U2gMLLFqXMp4LDgdSN_bI9dbVNnKOYtFurK6BNumjKYbo-neqGcvdrVNVmK-J_8UeuByC4By6aJqrNfn_in6BTo0gJ8</recordid><startdate>20130104</startdate><enddate>20130104</enddate><creator>Mo, Junming</creator><creator>Yang, Ruojie</creator><creator>Chen, Xingkuan</creator><creator>Tiwari, Bhoopendra</creator><creator>Chi, Yonggui Robin</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130104</creationdate><title>Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis</title><author>Mo, Junming ; Yang, Ruojie ; Chen, Xingkuan ; Tiwari, Bhoopendra ; Chi, Yonggui Robin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-f448b3186ba7d83e423a5afefe38a1f60c847d298a82c6e452b74aec5b2aef83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aldehydes - chemistry</topic><topic>Catalysis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Ketones - chemistry</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mo, Junming</creatorcontrib><creatorcontrib>Yang, Ruojie</creatorcontrib><creatorcontrib>Chen, Xingkuan</creatorcontrib><creatorcontrib>Tiwari, Bhoopendra</creatorcontrib><creatorcontrib>Chi, Yonggui Robin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mo, Junming</au><au>Yang, Ruojie</au><au>Chen, Xingkuan</au><au>Tiwari, Bhoopendra</au><au>Chi, Yonggui Robin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-01-04</date><risdate>2013</risdate><volume>15</volume><issue>1</issue><spage>50</spage><epage>53</epage><pages>50-53</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23249417</pmid><doi>10.1021/ol303035r</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2013-01, Vol.15 (1), p.50-53 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Aldehydes - chemistry Catalysis Heterocyclic Compounds - chemistry Ketones - chemistry Methane - analogs & derivatives Methane - chemistry Molecular Structure Oxidation-Reduction |
| title | Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis |
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