Functionalized cyclopentanes via Sc(III)-catalyzed intramolecular enolate alkylation

We report herein the intramolecular α-tert-alkylation of unsaturated β-ketoesters which gives rise to highly functionalized cyclopentanes. This transformation is characterized by its operational simplicity, mild reaction conditions and the use of scandium (III) triflate as a Lewis acid catalyst. Of...

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Veröffentlicht in:Tetrahedron 2018-06, Vol.74 (26), p.3306-3313
Hauptverfasser: McAtee, Christopher C., Ellinwood, Duncan C., McAtee, Rory C., Schindler, Corinna S.
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Sprache:eng
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Zusammenfassung:We report herein the intramolecular α-tert-alkylation of unsaturated β-ketoesters which gives rise to highly functionalized cyclopentanes. This transformation is characterized by its operational simplicity, mild reaction conditions and the use of scandium (III) triflate as a Lewis acid catalyst. Of interest, cyclopentanes bearing heterocycles, sites for post reaction functionalization and spirocyclic architectures are accessible with this strategy. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.04.036