Combined InCl3- and amine-catalyzed intramolecular addition of alpha-disubstituted aldehydes onto unactivated alkynes.
Identifieur interne : 001A75 ( Main/Exploration ); précédent : 001A74; suivant : 001A76Combined InCl3- and amine-catalyzed intramolecular addition of alpha-disubstituted aldehydes onto unactivated alkynes.
Auteurs : RBID : pubmed:20462188Abstract
The combination of enamine-type catalysis to the indium-catalyzed activation of alkynes allows the efficient preparation of functionalized cyclopentanes bearing a quaternary stereogenic center. A broad range of formylalkynyl derivatives has been prepared. The InCl(3)/(Cy)(i-Pr)NH system efficiently promotes the carbocyclization reaction of alpha-disubstituted aldehydes in good to excellent yields.
DOI: 10.1021/ol100729t
PubMed: 20462188
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Le document en format XML
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<author><name sortKey="Montaignac, Benjamin" uniqKey="Montaignac B">Benjamin Montaignac</name>
<affiliation wicri:level="3"><nlm:affiliation>ENSCP, Chimie ParisTech, UMR 7223, Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75231 Paris Cedex 05, France.</nlm:affiliation>
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<author><name sortKey="Vitale, Maxime R" uniqKey="Vitale M">Maxime R Vitale</name>
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<author><name sortKey="Michelet, Veronique" uniqKey="Michelet V">Veronique Michelet</name>
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<author><name sortKey="Ratovelomanana Vidal, Virginie" uniqKey="Ratovelomanana Vidal V">Virginie Ratovelomanana-Vidal</name>
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<front><div type="abstract" xml:lang="en">The combination of enamine-type catalysis to the indium-catalyzed activation of alkynes allows the efficient preparation of functionalized cyclopentanes bearing a quaternary stereogenic center. A broad range of formylalkynyl derivatives has been prepared. The InCl(3)/(Cy)(i-Pr)NH system efficiently promotes the carbocyclization reaction of alpha-disubstituted aldehydes in good to excellent yields.</div>
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<Title>Organic letters</Title>
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<Abstract><AbstractText>The combination of enamine-type catalysis to the indium-catalyzed activation of alkynes allows the efficient preparation of functionalized cyclopentanes bearing a quaternary stereogenic center. A broad range of formylalkynyl derivatives has been prepared. The InCl(3)/(Cy)(i-Pr)NH system efficiently promotes the carbocyclization reaction of alpha-disubstituted aldehydes in good to excellent yields.</AbstractText>
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