In Situ Catalyst Improvement in the Proline-Mediated α-Amination of Aldehydes
Kinetic investigations show that the proline-mediated α-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such tr...
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| Veröffentlicht in: | Journal of the American Chemical Society 2004-09, Vol.126 (38), p.11770-11771 |
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| container_end_page | 11771 |
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| container_issue | 38 |
| container_start_page | 11770 |
| container_title | Journal of the American Chemical Society |
| container_volume | 126 |
| creator | Iwamura, Hiroshi Mathew, Suju P Blackmond, Donna G |
| description | Kinetic investigations show that the proline-mediated α-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such transformations. The unusual characteristics exhibited by these reactions implicate amino acid catalysis in rationalizations of the origin of biological homochirality. |
| doi_str_mv | 10.1021/ja046258x |
| format | Article |
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Am. Chem. Soc</addtitle><description>Kinetic investigations show that the proline-mediated α-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such transformations. The unusual characteristics exhibited by these reactions implicate amino acid catalysis in rationalizations of the origin of biological homochirality.</description><subject>Aldehydes - chemistry</subject><subject>Amination</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Kinetics</subject><subject>Organic chemistry</subject><subject>Proline - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M2KFDEUBeAgitOOLnwByUbBRWn-KpUsm9ZxGlptmBHETbhVdcOkrZ8xSQ3Tj-WL-EyWdDO9cRUu-TgcDiEvOXvHmeDvd8CUFqW5f0QWvBSsKLnQj8mCMSaKymh5Rp6ltJtPJQx_Ss54KY0wVi7Il_VAr0Ke6AoydPuU6bq_jeMd9jhkGgaab5Bu49iFAYvP2AbI2NI_v4tlHwbIYRzo6Omya_Fm32J6Tp546BK-OL7n5NvFx-vVZbH5-mm9Wm4KkJXNheWVVFaWVWkQuLItsBZb5S0TRjbWNNZL6TnW3lesBmVqpY0SXkHtTamVPCdvDrlz118Tpuz6kBrsOhhwnJLT2lirhZ3h2wNs4phSRO9uY-gh7h1n7t947mG82b46hk51j-1JHteawesjgNRA5yMMTUgnp_lcU4rZFQcXUsb7h3-IP52uZFW66-2VE_z75Wb74Yezp1xoktuNUxzm7f5T8C9xTJHE</recordid><startdate>20040929</startdate><enddate>20040929</enddate><creator>Iwamura, Hiroshi</creator><creator>Mathew, Suju P</creator><creator>Blackmond, Donna G</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>20040929</creationdate><title>In Situ Catalyst Improvement in the Proline-Mediated α-Amination of Aldehydes</title><author>Iwamura, Hiroshi ; Mathew, Suju P ; Blackmond, Donna G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-91734935758ea149da0ded4f90283c98c9f33f1ebff70ba48b46842f4abf85643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Aldehydes - chemistry</topic><topic>Amination</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Kinetics</topic><topic>Organic chemistry</topic><topic>Proline - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Iwamura, Hiroshi</creatorcontrib><creatorcontrib>Mathew, Suju P</creatorcontrib><creatorcontrib>Blackmond, Donna G</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Iwamura, Hiroshi</au><au>Mathew, Suju P</au><au>Blackmond, Donna G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In Situ Catalyst Improvement in the Proline-Mediated α-Amination of Aldehydes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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| ispartof | Journal of the American Chemical Society, 2004-09, Vol.126 (38), p.11770-11771 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Aldehydes - chemistry Amination Catalysis Chemistry Exact sciences and technology Kinetics Organic chemistry Proline - chemistry |
| title | In Situ Catalyst Improvement in the Proline-Mediated α-Amination of Aldehydes |
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