The Vinylogous Aldol Reaction of Unsaturated Esters and Enolizable Aldehydes Using the Novel Lewis Acid Aluminum Tris(2,6-di-2-naphthylphenoxide)
Identifieur interne : 000235 ( Ncbi/Merge ); précédent : 000234; suivant : 000236The Vinylogous Aldol Reaction of Unsaturated Esters and Enolizable Aldehydes Using the Novel Lewis Acid Aluminum Tris(2,6-di-2-naphthylphenoxide)
Auteurs : Jeffrey A. Gazaille ; Tarek SammakiaSource :
- Organic letters [ 1523-7060 ] ; 2012.
Abstract
The synthesis of the novel Lewis acid, aluminum tris(2,6-di-2-naphthylphenoxide) (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto’s Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups more effectively block the α-position of aldehydes, enabling the selective enolization of crotonate esters in the presence of enolizable aldehydes. Vinylogous aldol reactions then proceed smoothly and in high yields with a variety of substrates.
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DOI: 10.1021/ol300738f
PubMed: 22621176
PubMed Central: 3427784
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<pmc-dir>properties manuscript</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-journal-id">100890393</journal-id><journal-id journal-id-type="pubmed-jr-id">21677</journal-id><journal-id journal-id-type="nlm-ta">Org Lett</journal-id><journal-id journal-id-type="iso-abbrev">Org. Lett.</journal-id><journal-title-group><journal-title>Organic letters</journal-title></journal-title-group><issn pub-type="ppub">1523-7060</issn><issn pub-type="epub">1523-7052</issn></journal-meta><article-meta><article-id pub-id-type="pmid">22621176</article-id><article-id pub-id-type="pmc">3427784</article-id><article-id pub-id-type="doi">10.1021/ol300738f</article-id><article-id pub-id-type="manuscript">NIHMS380032</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>The Vinylogous Aldol Reaction of Unsaturated Esters and Enolizable Aldehydes Using the Novel Lewis Acid Aluminum Tris(2,6-di-2-naphthylphenoxide)</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Gazaille</surname><given-names>Jeffrey A.</given-names></name></contrib><contrib contrib-type="author" corresp="yes"><name><surname>Sammakia</surname><given-names>Tarek</given-names></name><email>sammakia@colorado.edu</email></contrib><aff id="A1">Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215</aff></contrib-group><pub-date pub-type="nihms-submitted"><day>25</day><month>5</month><year>2012</year></pub-date><pub-date pub-type="epub"><day>23</day><month>5</month><year>2012</year></pub-date><pub-date pub-type="ppub"><day>1</day><month>6</month><year>2012</year></pub-date><pub-date pub-type="pmc-release"><day>01</day><month>6</month><year>2013</year></pub-date><volume>14</volume><issue>11</issue><fpage>2678</fpage><lpage>2681</lpage><abstract><p id="P1"><graphic xlink:href="nihms380032f4.jpg" position="anchor" orientation="portrait"></graphic></p><p id="P2">The synthesis of the novel Lewis acid, aluminum tris(2,6-di-2-naphthylphenoxide) (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto’s Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups more effectively block the α-position of aldehydes, enabling the selective enolization of crotonate esters in the presence of enolizable aldehydes. Vinylogous aldol reactions then proceed smoothly and in high yields with a variety of substrates.</p></abstract></article-meta></front></pmc><affiliations><list></list><tree><noCountry><name sortKey="Gazaille, Jeffrey A" sort="Gazaille, Jeffrey A" uniqKey="Gazaille J" first="Jeffrey A." last="Gazaille">Jeffrey A. Gazaille</name><name sortKey="Sammakia, Tarek" sort="Sammakia, Tarek" uniqKey="Sammakia T" first="Tarek" last="Sammakia">Tarek Sammakia</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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