Novel aminoimidazole derived proline organocatalysts for aldol reactions
A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high s...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron 2012-12, Vol.68 (49), p.10230-10235 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 10235 |
|---|---|
| container_issue | 49 |
| container_start_page | 10230 |
| container_title | Tetrahedron |
| container_volume | 68 |
| creator | Tang, Gongkun Gün, Ümit Altenbach, Hans-Josef |
| description | A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high selectivities (ee 98%, de 98/2) were obtained in intermolecular aldol reaction even with only 1 equiv of ketone. Likewise, these systems also can catalyze intramolecular aldol reactions with good results.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2012.09.071 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744705152</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402012014615</els_id><sourcerecordid>1744705152</sourcerecordid><originalsourceid>FETCH-LOGICAL-c360t-582dac8f054f56af13f9d4650d2c4ad934926935fd332cd113fab06652162a463</originalsourceid><addsrcrecordid>eNp9kEFLAzEQhYMoWKs_wNteBC-7TrJJ2sWTiFpB9KLnMCYTSUk3mqyF-uvd0uLR0xzmvTdvPsbOOTQcuL5aNgMNjQAuGugamPEDNuFSy1pJrg_ZBEBCLUHAMTspZQkAnIt2whbPaU2xwlXoU1gFhz8pUuUohzW56jOnGHqqUv7APlkcMG7KUCqfcoXRpVhlQjuE1JdTduQxFjrbzyl7u797vV3UTy8Pj7c3T7VtNQy1mguHdu5BSa80et76zkmtwAkr0XWt7ITuWuVd2wrr-LjHd9BaCa4FSt1O2eUud-z29U1lMKtQLMWIPaXvYvhMyhkorsQo5TupzamUTN585rDCvDEczJaaWZqRmtlSM9CZkdroudjHY7EYfcbehvJnFHqsoOfbGtc7HY2_rgNlU2yg3pILmexgXAr_XPkFbaCCHA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744705152</pqid></control><display><type>article</type><title>Novel aminoimidazole derived proline organocatalysts for aldol reactions</title><source>Elsevier ScienceDirect Journals Complete</source><creator>Tang, Gongkun ; Gün, Ümit ; Altenbach, Hans-Josef</creator><creatorcontrib>Tang, Gongkun ; Gün, Ümit ; Altenbach, Hans-Josef</creatorcontrib><description>A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high selectivities (ee 98%, de 98/2) were obtained in intermolecular aldol reaction even with only 1 equiv of ketone. Likewise, these systems also can catalyze intramolecular aldol reactions with good results.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2012.09.071</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Aldehydes ; Aldol reaction ; Amides ; Carbonyl groups ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Enantioselectivity ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Imidazole ; Ketones ; Organic chemistry ; Organocatalysis ; Preparations and properties ; Proline ; Selectivity ; Tetrahedrons ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Tetrahedron, 2012-12, Vol.68 (49), p.10230-10235</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-582dac8f054f56af13f9d4650d2c4ad934926935fd332cd113fab06652162a463</citedby><cites>FETCH-LOGICAL-c360t-582dac8f054f56af13f9d4650d2c4ad934926935fd332cd113fab06652162a463</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2012.09.071$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26463686$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Tang, Gongkun</creatorcontrib><creatorcontrib>Gün, Ümit</creatorcontrib><creatorcontrib>Altenbach, Hans-Josef</creatorcontrib><title>Novel aminoimidazole derived proline organocatalysts for aldol reactions</title><title>Tetrahedron</title><description>A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high selectivities (ee 98%, de 98/2) were obtained in intermolecular aldol reaction even with only 1 equiv of ketone. Likewise, these systems also can catalyze intramolecular aldol reactions with good results.
[Display omitted]</description><subject>Aldehydes</subject><subject>Aldol reaction</subject><subject>Amides</subject><subject>Carbonyl groups</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Enantioselectivity</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Imidazole</subject><subject>Ketones</subject><subject>Organic chemistry</subject><subject>Organocatalysis</subject><subject>Preparations and properties</subject><subject>Proline</subject><subject>Selectivity</subject><subject>Tetrahedrons</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kEFLAzEQhYMoWKs_wNteBC-7TrJJ2sWTiFpB9KLnMCYTSUk3mqyF-uvd0uLR0xzmvTdvPsbOOTQcuL5aNgMNjQAuGugamPEDNuFSy1pJrg_ZBEBCLUHAMTspZQkAnIt2whbPaU2xwlXoU1gFhz8pUuUohzW56jOnGHqqUv7APlkcMG7KUCqfcoXRpVhlQjuE1JdTduQxFjrbzyl7u797vV3UTy8Pj7c3T7VtNQy1mguHdu5BSa80et76zkmtwAkr0XWt7ITuWuVd2wrr-LjHd9BaCa4FSt1O2eUud-z29U1lMKtQLMWIPaXvYvhMyhkorsQo5TupzamUTN585rDCvDEczJaaWZqRmtlSM9CZkdroudjHY7EYfcbehvJnFHqsoOfbGtc7HY2_rgNlU2yg3pILmexgXAr_XPkFbaCCHA</recordid><startdate>20121209</startdate><enddate>20121209</enddate><creator>Tang, Gongkun</creator><creator>Gün, Ümit</creator><creator>Altenbach, Hans-Josef</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20121209</creationdate><title>Novel aminoimidazole derived proline organocatalysts for aldol reactions</title><author>Tang, Gongkun ; Gün, Ümit ; Altenbach, Hans-Josef</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-582dac8f054f56af13f9d4650d2c4ad934926935fd332cd113fab06652162a463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aldehydes</topic><topic>Aldol reaction</topic><topic>Amides</topic><topic>Carbonyl groups</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Enantioselectivity</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Imidazole</topic><topic>Ketones</topic><topic>Organic chemistry</topic><topic>Organocatalysis</topic><topic>Preparations and properties</topic><topic>Proline</topic><topic>Selectivity</topic><topic>Tetrahedrons</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tang, Gongkun</creatorcontrib><creatorcontrib>Gün, Ümit</creatorcontrib><creatorcontrib>Altenbach, Hans-Josef</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology 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>Tang, Gongkun</au><au>Gün, Ümit</au><au>Altenbach, Hans-Josef</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel aminoimidazole derived proline organocatalysts for aldol reactions</atitle><jtitle>Tetrahedron</jtitle><date>2012-12-09</date><risdate>2012</risdate><volume>68</volume><issue>49</issue><spage>10230</spage><epage>10235</epage><pages>10230-10235</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high selectivities (ee 98%, de 98/2) were obtained in intermolecular aldol reaction even with only 1 equiv of ketone. Likewise, these systems also can catalyze intramolecular aldol reactions with good results.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2012.09.071</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2012-12, Vol.68 (49), p.10230-10235 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744705152 |
| source | Elsevier ScienceDirect Journals Complete |
| subjects | Aldehydes Aldol reaction Amides Carbonyl groups Catalysis Catalysts: preparations and properties Chemistry Enantioselectivity Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Imidazole Ketones Organic chemistry Organocatalysis Preparations and properties Proline Selectivity Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Novel aminoimidazole derived proline organocatalysts for aldol reactions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T03%3A20%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Novel%20aminoimidazole%20derived%20proline%20organocatalysts%20for%20aldol%20reactions&rft.jtitle=Tetrahedron&rft.au=Tang,%20Gongkun&rft.date=2012-12-09&rft.volume=68&rft.issue=49&rft.spage=10230&rft.epage=10235&rft.pages=10230-10235&rft.issn=0040-4020&rft.eissn=1464-5416&rft.coden=TETRAB&rft_id=info:doi/10.1016/j.tet.2012.09.071&rft_dat=%3Cproquest_cross%3E1744705152%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1744705152&rft_id=info:pmid/&rft_els_id=S0040402012014615&rfr_iscdi=true |