Thermal [2 + 2]-Cycloaddition of Ketenes with Chiral Enol Ethers: Route to Densely Substituted Cyclobutanones

Access to chiral polysubstituted cyclobutanones by [2 + 2]-cycloaddition of ketenes with chiral acyclic enol ethers is reported. A wide variety of easily accessible di- and monosubstituted ketenes were found to react with a very high degree of stereoselectivity with chiral, Stericol derived, acyclic...

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Veröffentlicht in:Organic letters 2016-06, Vol.18 (12), p.2824-2827
Hauptverfasser: Rullière, Pauline, Grisel, Julien, Poittevin, Clément, Cividino, Pascale, Carret, Sébastien, Poisson, Jean-François
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Sprache:eng
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Zusammenfassung:Access to chiral polysubstituted cyclobutanones by [2 + 2]-cycloaddition of ketenes with chiral acyclic enol ethers is reported. A wide variety of easily accessible di- and monosubstituted ketenes were found to react with a very high degree of stereoselectivity with chiral, Stericol derived, acyclic enol ethers. This combination of simple reagents provides straightforward entry to highly substituted enantioenriched cyclobutanones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01058