Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives
A new method for the synthesis of β-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicat...
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| Veröffentlicht in: | Organic letters 2004-09, Vol.6 (20), p.3553-3556 |
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| creator | Ege, Markus Wanner, Klaus T |
| description | A new method for the synthesis of β-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the β-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine. |
| doi_str_mv | 10.1021/ol0485518 |
| format | Article |
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Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the β-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0485518</identifier><identifier>PMID: 15387546</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amino Acids - chemical synthesis ; Catalysis ; Indicators and Reagents ; Molecular Structure ; Oxidation-Reduction ; Pyridones - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2004-09, Vol.6 (20), p.3553-3556</ispartof><rights>Copyright © 2004 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-170235baedbcfc892aea20444042aa91c3f5b14cb90a6cbf2539b63e6d9696293</citedby><cites>FETCH-LOGICAL-a311t-170235baedbcfc892aea20444042aa91c3f5b14cb90a6cbf2539b63e6d9696293</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol0485518$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0485518$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15387546$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ege, Markus</creatorcontrib><creatorcontrib>Wanner, Klaus T</creatorcontrib><title>Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new method for the synthesis of β-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the β-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.</description><subject>Amino Acids - chemical synthesis</subject><subject>Catalysis</subject><subject>Indicators and Reagents</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Pyridones - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EtOwzAQBmALgWgpLLgA8gYkFgE_YidelpaXVKkLHtvIsR3qKomLnVTkWhyEM5HSCjasZjT69EvzA3CK0RVGBF-7EsUpYzjdA0PMCI0SxMj-787RAByFsEQI9xdxCAaY0TRhMR-C16eubhYm2ABdAb8-o3FlawfHyuoAb2QwGroazj-slo1dGzgpjVzLN7PRU7votHerzlvtagOnxtv1DwvH4KCQZTAnuzkCL3e3z5OHaDa_f5yMZ5GkGDcRThChLJdG56pQqSDSSILiOEYxkVJgRQuW41jlAkmu8oIwKnJODdeCC04EHYGLbe7Ku_fWhCarbFCmLGVtXBsyzgXiCeY9vNxC5V0I3hTZyttK-i7DKNuUmP2W2NuzXWibV0b_yV1rPTjfAqlCtnStr_sf_wn6BlPveK0</recordid><startdate>20040930</startdate><enddate>20040930</enddate><creator>Ege, Markus</creator><creator>Wanner, Klaus T</creator><general>American Chemical Society</general><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>20040930</creationdate><title>Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives</title><author>Ege, Markus ; Wanner, Klaus T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-170235baedbcfc892aea20444042aa91c3f5b14cb90a6cbf2539b63e6d9696293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Amino Acids - chemical synthesis</topic><topic>Catalysis</topic><topic>Indicators and Reagents</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Pyridones - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ege, Markus</creatorcontrib><creatorcontrib>Wanner, Klaus T</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ege, Markus</au><au>Wanner, Klaus T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2004-09-30</date><risdate>2004</risdate><volume>6</volume><issue>20</issue><spage>3553</spage><epage>3556</epage><pages>3553-3556</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new method for the synthesis of β-amino acids based on 2,3-dihydropyridones as starting materials is presented. Conversions of 2,3-dihydropyridones with NaIO4 and subsequently with base gave the corresponding β-amino acids in a one-pot procedure. The reactions have been monitored by 1H NMR indicating that the β-amino acids were formed in quantitative yields mostly. This method appears to be of broad scope, as 2-substituted 2,3-dihydropyridones are easily accessible via N-acyliminium ions generated from 4-methoxypyridine.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15387546</pmid><doi>10.1021/ol0485518</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Amino Acids - chemical synthesis Catalysis Indicators and Reagents Molecular Structure Oxidation-Reduction Pyridones - chemistry Stereoisomerism |
| title | Synthesis of β-Amino Acids Based on Oxidative Cleavage of Dihydropyridone Derivatives |
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