Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde
For the first time, the l-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the fo...
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| Veröffentlicht in: | Journal of organic chemistry 2002-01, Vol.67 (1), p.301-303 |
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| container_end_page | 303 |
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| container_title | Journal of organic chemistry |
| container_volume | 67 |
| creator | Córdova, Armando Notz, Wolfgang Barbas, Carlos F |
| description | For the first time, the l-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the formation of 2 is proposed. |
| doi_str_mv | 10.1021/jo015881m |
| format | Article |
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Further transformations of 2 into synthetically valuable building blocks are presented. 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Org. Chem</addtitle><description>For the first time, the l-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the formation of 2 is proposed.</description><subject>Acetaldehyde - chemistry</subject><subject>Aldehydes - chemical synthesis</subject><subject>Aliphatic compounds</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Proline - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtuEzEUBmALUdG0dMELoNmA2oWLPb6NlyHqhapSLykbWFgnnjPKlLmk9kTK8PQYJWo29cay_PnX8U_IJ87OOcv5t-eecVUUvH1HJlzljGrL5HsyYSzPqci1OCRHMT6ztJRSH8gh58YYacyE_L4PfVN3SGcwQDP-xTK7S6f5gKtsGse2xSHUPpuP3bDEWMesrzJFr8cy9JuRnuYXZ3SJG-ygyarQt9nUY8opcTmW-JEcVNBEPNntx-Tn5cXT7Jre3l39mE1vKUipBpqLyiwM2IrLBVptRalAaFsYqSshoUReMrQCoGCQ_uKt5boA661iIj3R4ph83eauQv-yxji4to4emwY67NfRGS6UkqpI8GwLfehjDFi5VahbCKPjzP1v0r02meznXeh60WK5l7vqEviyAxA9NFWAztdx74QUkkuWHN26Og64eb2H8MdpI4xyT_dzp29-XT58f3h0V_tc8DHNsw6p2_jGgP8AXceVKg</recordid><startdate>20020111</startdate><enddate>20020111</enddate><creator>Córdova, Armando</creator><creator>Notz, Wolfgang</creator><creator>Barbas, Carlos F</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>20020111</creationdate><title>Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde</title><author>Córdova, Armando ; Notz, Wolfgang ; Barbas, Carlos F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-23f7b7a9f14be9693d5a3698746f34ade1d0e93aa80a263c99168a9c950314b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Acetaldehyde - chemistry</topic><topic>Aldehydes - chemical synthesis</topic><topic>Aliphatic compounds</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Proline - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Córdova, Armando</creatorcontrib><creatorcontrib>Notz, Wolfgang</creatorcontrib><creatorcontrib>Barbas, Carlos F</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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Córdova, Armando</au><au>Notz, Wolfgang</au><au>Barbas, Carlos F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-01-11</date><risdate>2002</risdate><volume>67</volume><issue>1</issue><spage>301</spage><epage>303</epage><pages>301-303</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>For the first time, the l-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the formation of 2 is proposed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11777477</pmid><doi>10.1021/jo015881m</doi><tpages>3</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2002-01, Vol.67 (1), p.301-303 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Acetaldehyde - chemistry Aldehydes - chemical synthesis Aliphatic compounds Catalysis Chemistry Exact sciences and technology Organic chemistry Preparations and properties Proline - chemistry Stereoisomerism |
| title | Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde |
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