Supported l-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition
Zirconium phosphates methyl and/or phenyl phosphonates-supported l-proline have been prepared as amorphous solids and their catalytic activity tested on the direct asymmetric aldol addition of cyclohexanone to p-nitrobenzaldehyde in DMF/H 2O (9:1) and in sole water. [Display omitted] ► Zirconium pho...
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| Veröffentlicht in: | Journal of catalysis 2011-08, Vol.282 (1), p.112-119 |
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| container_title | Journal of catalysis |
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| creator | Calogero, Salvatore Lanari, Daniela Orrù, Mara Piermatti, Oriana Pizzo, Ferdinando Vaccaro, Luigi |
| description | Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids and their catalytic activity tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water.
[Display omitted]
► Zirconium phosphate/phosphonates-supported
l-proline have been prepared. ► The solids tested on the asymmetric aldol addition in DMF/H
2O 9:1 and in water. ► The hydrophobic groups on solid catalyst surface increasing the catalytic activity. ► High diastereoselectivity and high enantiomeric excess have been obtained.
Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids by precipitation of (4
R)-4-(phosphonooxy)-
l-proline, methyl and/or phenyl phosphonic acid with ZrOCl
2. The supported
l-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water. The hydrophobic groups on solid surface favor reagents’ diffusion toward proline chiral moiety increasing the catalytic activity of supported
l-proline. High diastereoselectivity (
anti/syn up to 94:6) and high enantiomeric excess up to 97% have been obtained. |
| doi_str_mv | 10.1016/j.jcat.2011.06.004 |
| format | Article |
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l-proline have been prepared as amorphous solids and their catalytic activity tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water.
[Display omitted]
► Zirconium phosphate/phosphonates-supported
l-proline have been prepared. ► The solids tested on the asymmetric aldol addition in DMF/H
2O 9:1 and in water. ► The hydrophobic groups on solid catalyst surface increasing the catalytic activity. ► High diastereoselectivity and high enantiomeric excess have been obtained.
Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids by precipitation of (4
R)-4-(phosphonooxy)-
l-proline, methyl and/or phenyl phosphonic acid with ZrOCl
2. The supported
l-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water. The hydrophobic groups on solid surface favor reagents’ diffusion toward proline chiral moiety increasing the catalytic activity of supported
l-proline. High diastereoselectivity (
anti/syn up to 94:6) and high enantiomeric excess up to 97% have been obtained.</description><identifier>ISSN: 0021-9517</identifier><identifier>EISSN: 1090-2694</identifier><identifier>DOI: 10.1016/j.jcat.2011.06.004</identifier><identifier>CODEN: JCTLA5</identifier><language>eng</language><publisher>Amsterdam: Elsevier Inc</publisher><subject>Aldol addition ; Aqueous medium ; Catalysis ; Catalysts ; catalytic activity ; Chemistry ; Chiral heterogeneous catalysts ; cyclohexanones ; Exact sciences and technology ; General and physical chemistry ; hydrophobicity ; Phosphates ; phosphonates ; phosphorous acid ; proline ; Supported l-proline ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ; Zirconium ; Zirconium phosphates</subject><ispartof>Journal of catalysis, 2011-08, Vol.282 (1), p.112-119</ispartof><rights>2011 Elsevier Inc.</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-433a8647d8cb5ef98de74d1bbe54d40ea9dcece89a3a6c47b7df8a14a330742a3</citedby><cites>FETCH-LOGICAL-c381t-433a8647d8cb5ef98de74d1bbe54d40ea9dcece89a3a6c47b7df8a14a330742a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jcat.2011.06.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24427878$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Calogero, Salvatore</creatorcontrib><creatorcontrib>Lanari, Daniela</creatorcontrib><creatorcontrib>Orrù, Mara</creatorcontrib><creatorcontrib>Piermatti, Oriana</creatorcontrib><creatorcontrib>Pizzo, Ferdinando</creatorcontrib><creatorcontrib>Vaccaro, Luigi</creatorcontrib><title>Supported l-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition</title><title>Journal of catalysis</title><description>Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids and their catalytic activity tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water.
[Display omitted]
► Zirconium phosphate/phosphonates-supported
l-proline have been prepared. ► The solids tested on the asymmetric aldol addition in DMF/H
2O 9:1 and in water. ► The hydrophobic groups on solid catalyst surface increasing the catalytic activity. ► High diastereoselectivity and high enantiomeric excess have been obtained.
Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids by precipitation of (4
R)-4-(phosphonooxy)-
l-proline, methyl and/or phenyl phosphonic acid with ZrOCl
2. The supported
l-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water. The hydrophobic groups on solid surface favor reagents’ diffusion toward proline chiral moiety increasing the catalytic activity of supported
l-proline. High diastereoselectivity (
anti/syn up to 94:6) and high enantiomeric excess up to 97% have been obtained.</description><subject>Aldol addition</subject><subject>Aqueous medium</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>catalytic activity</subject><subject>Chemistry</subject><subject>Chiral heterogeneous catalysts</subject><subject>cyclohexanones</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>hydrophobicity</subject><subject>Phosphates</subject><subject>phosphonates</subject><subject>phosphorous acid</subject><subject>proline</subject><subject>Supported l-proline</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Zirconium</subject><subject>Zirconium phosphates</subject><issn>0021-9517</issn><issn>1090-2694</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kc9u1DAQhy0EEkvhBbhgIXFMajtO4khcUMWfSpU4lJ6tWXuy6yhrB9tBWl6DF8ZLKo49WdZ88_PMZ0LeclZzxrvrqZ4M5FowzmvW1YzJZ2TH2cAq0Q3yOdkxJng1tLx_SV6lNLECtq3akT_367KEmNHSuVpimJ1HGjz97aIJ3q0nuhxDWo6QMdET5uN5puDtdYilgL7ctnrw_whI9IgZYzigx7AmGuIBfCizwXxOOdGxNFoX0eTCnk8lMTpDYbah5Frrsgv-NXkxwpzwzeN5RR6-fP5x8626-_719ubTXWUaxXMlmwZUJ3urzL7FcVAWe2n5fo-ttJIhDNagQTVAA52R_b63owIuoWlYLwU0V-T9llv2_rliynoKa_TlSa0UE0yIRhVIbJCJIaWIo16iO0E8a870xb2e9MW9vrjXrNPFfWn68JgMycA8RvDGpf-dQkrRq_4S_m7jRggaDrEwD_clqGPlg2TH2kJ83AgsIn45jDoZh97gJlHb4J4a5C-sS6iR</recordid><startdate>20110815</startdate><enddate>20110815</enddate><creator>Calogero, Salvatore</creator><creator>Lanari, Daniela</creator><creator>Orrù, Mara</creator><creator>Piermatti, Oriana</creator><creator>Pizzo, Ferdinando</creator><creator>Vaccaro, Luigi</creator><general>Elsevier Inc</general><general>Elsevier</general><general>Elsevier BV</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20110815</creationdate><title>Supported l-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition</title><author>Calogero, Salvatore ; Lanari, Daniela ; Orrù, Mara ; Piermatti, Oriana ; Pizzo, Ferdinando ; Vaccaro, Luigi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-433a8647d8cb5ef98de74d1bbe54d40ea9dcece89a3a6c47b7df8a14a330742a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aldol addition</topic><topic>Aqueous medium</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>catalytic activity</topic><topic>Chemistry</topic><topic>Chiral heterogeneous catalysts</topic><topic>cyclohexanones</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>hydrophobicity</topic><topic>Phosphates</topic><topic>phosphonates</topic><topic>phosphorous acid</topic><topic>proline</topic><topic>Supported l-proline</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Zirconium</topic><topic>Zirconium phosphates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Calogero, Salvatore</creatorcontrib><creatorcontrib>Lanari, Daniela</creatorcontrib><creatorcontrib>Orrù, Mara</creatorcontrib><creatorcontrib>Piermatti, Oriana</creatorcontrib><creatorcontrib>Pizzo, Ferdinando</creatorcontrib><creatorcontrib>Vaccaro, Luigi</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Calogero, Salvatore</au><au>Lanari, Daniela</au><au>Orrù, Mara</au><au>Piermatti, Oriana</au><au>Pizzo, Ferdinando</au><au>Vaccaro, Luigi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Supported l-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition</atitle><jtitle>Journal of catalysis</jtitle><date>2011-08-15</date><risdate>2011</risdate><volume>282</volume><issue>1</issue><spage>112</spage><epage>119</epage><pages>112-119</pages><issn>0021-9517</issn><eissn>1090-2694</eissn><coden>JCTLA5</coden><abstract>Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids and their catalytic activity tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water.
[Display omitted]
► Zirconium phosphate/phosphonates-supported
l-proline have been prepared. ► The solids tested on the asymmetric aldol addition in DMF/H
2O 9:1 and in water. ► The hydrophobic groups on solid catalyst surface increasing the catalytic activity. ► High diastereoselectivity and high enantiomeric excess have been obtained.
Zirconium phosphates methyl and/or phenyl phosphonates-supported
l-proline have been prepared as amorphous solids by precipitation of (4
R)-4-(phosphonooxy)-
l-proline, methyl and/or phenyl phosphonic acid with ZrOCl
2. The supported
l-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to
p-nitrobenzaldehyde in DMF/H
2O (9:1) and in sole water. The hydrophobic groups on solid surface favor reagents’ diffusion toward proline chiral moiety increasing the catalytic activity of supported
l-proline. High diastereoselectivity (
anti/syn up to 94:6) and high enantiomeric excess up to 97% have been obtained.</abstract><cop>Amsterdam</cop><pub>Elsevier Inc</pub><doi>10.1016/j.jcat.2011.06.004</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of catalysis, 2011-08, Vol.282 (1), p.112-119 |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Aldol addition Aqueous medium Catalysis Catalysts catalytic activity Chemistry Chiral heterogeneous catalysts cyclohexanones Exact sciences and technology General and physical chemistry hydrophobicity Phosphates phosphonates phosphorous acid proline Supported l-proline Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Zirconium Zirconium phosphates |
| title | Supported l-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition |
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