The Vinylogous Aldol Reaction of Unsaturated Esters and Enolizable Aldehydes Using the Novel Lewis Acid Aluminum Tris(2,6-di-2-naphthylphenoxide)
Identifieur interne : 000045 ( Pmc/Checkpoint ); précédent : 000044; suivant : 000046The 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.
Url:
DOI: 10.1021/ol300738f
PubMed: 22621176
PubMed Central: 3427784
Affiliations:
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PMC:3427784Le document en format XML
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<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>
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<contrib-group><contrib contrib-type="author"><name><surname>Gazaille</surname>
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<given-names>Tarek</given-names>
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<email>sammakia@colorado.edu</email>
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<aff id="A1">Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215</aff>
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<pub-date pub-type="nihms-submitted"><day>25</day>
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<volume>14</volume>
<issue>11</issue>
<fpage>2678</fpage>
<lpage>2681</lpage>
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<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>
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