Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions
The self-assembling gold nanoparticle (GNP)-supported l-proline derivative, which was readily synthesized in four steps from 4-hydroxy-l-proline and chloroauric acid, was used for enamine-based aldol reactions. The modified Brust-Schiffrin (BS) synthesis was favored over the ligand exchange reaction...
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| Veröffentlicht in: | Tetrahedron 2016-04, Vol.72 (16), p.1984-1990 |
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| container_end_page | 1990 |
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| container_issue | 16 |
| container_start_page | 1984 |
| container_title | Tetrahedron |
| container_volume | 72 |
| creator | Sóti, Péter Lajos Yamashita, Hiroki Sato, Kohei Narumi, Tetsuo Toda, Mitsuo Watanabe, Naoharu Marosi, György Mase, Nobuyuki |
| description | The self-assembling gold nanoparticle (GNP)-supported l-proline derivative, which was readily synthesized in four steps from 4-hydroxy-l-proline and chloroauric acid, was used for enamine-based aldol reactions. The modified Brust-Schiffrin (BS) synthesis was favored over the ligand exchange reaction in order to develop a new and simple synthetic pathway for nanoparticle-supported catalyst. Use of immobilized organocatalyst on nanoscale solid carrier led to excellent selectivities (up to 94:6 dr and 94% ee) in asymmetric reactions of ketones and benzaldehydes. GNPs operate under pseudo-homogeneous conditions which are easily recycled and reused at least five times without significant loss of weight, activity, diastereo- and enantioselectivities.
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| doi_str_mv | 10.1016/j.tet.2016.02.065 |
| format | Article |
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[Display omitted]</description><subject>Aldehydes</subject><subject>Aldol reaction</subject><subject>Asymmetry</subject><subject>Derivatives</subject><subject>Gold</subject><subject>Ligands</subject><subject>Nanoparticle</subject><subject>Nanostructure</subject><subject>Organocatalyst</subject><subject>Recycled</subject><subject>Supported catalysis</subject><subject>Synthesis (chemistry)</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kMFu2zAMhoVhBZale4DddOzFHmXLmoOeimLrChTYYdtZYGQ6UyBLrqgUyNtPRXbuiQT5fwT4CfFZQatAmS_HtlBpu9q20LVghndio7TRzaCVeS82ABoaDR18EB-ZjwCgVNdvxMuvcyx_iT3LNEuUTGFukJmWffDxIA8pTDJiTCvm4l2ghk_rmnKhSaZ8qAuHBcOZi5xTlhRx8ZGaPXINIJ-XhUr2TmKYUpCZ0BWfIl-LqxkD06f_dSv-fP_2-_5H8_Tz4fH-7qlxWkNpvu7U0Gszj7Abzejc4DTqzgHOO6X3exgnIOh7mMjR3CujeqPVUCejcdOA1G_FzeXumtPzibjYxbOjEDBSOrFVozKgh74iW6EuUZcTc6bZrtkvmM9WgX11bI-2Oravji10tjquzO2FofrDi6ds2XmKjiafyRU7Jf8G_Q-tcYbV</recordid><startdate>20160421</startdate><enddate>20160421</enddate><creator>Sóti, Péter Lajos</creator><creator>Yamashita, Hiroki</creator><creator>Sato, Kohei</creator><creator>Narumi, Tetsuo</creator><creator>Toda, Mitsuo</creator><creator>Watanabe, Naoharu</creator><creator>Marosi, György</creator><creator>Mase, Nobuyuki</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>20160421</creationdate><title>Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions</title><author>Sóti, Péter Lajos ; Yamashita, Hiroki ; Sato, Kohei ; Narumi, Tetsuo ; Toda, Mitsuo ; Watanabe, Naoharu ; Marosi, György ; Mase, Nobuyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c440t-7915346f809868cc5c4a42c0af914bb08d0e0330decef31613641503386cd5ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Aldehydes</topic><topic>Aldol reaction</topic><topic>Asymmetry</topic><topic>Derivatives</topic><topic>Gold</topic><topic>Ligands</topic><topic>Nanoparticle</topic><topic>Nanostructure</topic><topic>Organocatalyst</topic><topic>Recycled</topic><topic>Supported catalysis</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sóti, Péter Lajos</creatorcontrib><creatorcontrib>Yamashita, Hiroki</creatorcontrib><creatorcontrib>Sato, Kohei</creatorcontrib><creatorcontrib>Narumi, Tetsuo</creatorcontrib><creatorcontrib>Toda, Mitsuo</creatorcontrib><creatorcontrib>Watanabe, Naoharu</creatorcontrib><creatorcontrib>Marosi, György</creatorcontrib><creatorcontrib>Mase, Nobuyuki</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>Sóti, Péter Lajos</au><au>Yamashita, Hiroki</au><au>Sato, Kohei</au><au>Narumi, Tetsuo</au><au>Toda, Mitsuo</au><au>Watanabe, Naoharu</au><au>Marosi, György</au><au>Mase, Nobuyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions</atitle><jtitle>Tetrahedron</jtitle><date>2016-04-21</date><risdate>2016</risdate><volume>72</volume><issue>16</issue><spage>1984</spage><epage>1990</epage><pages>1984-1990</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>The self-assembling gold nanoparticle (GNP)-supported l-proline derivative, which was readily synthesized in four steps from 4-hydroxy-l-proline and chloroauric acid, was used for enamine-based aldol reactions. The modified Brust-Schiffrin (BS) synthesis was favored over the ligand exchange reaction in order to develop a new and simple synthetic pathway for nanoparticle-supported catalyst. Use of immobilized organocatalyst on nanoscale solid carrier led to excellent selectivities (up to 94:6 dr and 94% ee) in asymmetric reactions of ketones and benzaldehydes. GNPs operate under pseudo-homogeneous conditions which are easily recycled and reused at least five times without significant loss of weight, activity, diastereo- and enantioselectivities.
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| fulltext | fulltext |
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| ispartof | Tetrahedron, 2016-04, Vol.72 (16), p.1984-1990 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Aldehydes Aldol reaction Asymmetry Derivatives Gold Ligands Nanoparticle Nanostructure Organocatalyst Recycled Supported catalysis Synthesis (chemistry) |
| title | Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions |
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