Functionalized cyclopentanes via Sc(III)-catalyzed intramolecular enolate alkylation. Issue 26 (28th June 2018)

• Record Type: Journal Article
• Authors: McAtee, Christopher C.; Ellinwood, Duncan C.; McAtee, Rory C.; Schindler, Corinna S.
• Is Part Of: Tetrahedron. Volume 74:Issue 26(2018)
• Page Start: 3306
• Page End: 3313
• Publication Date: 2018-06-28
• Subjects: Scandium(III) triflate -- Functionalized cyclopentanes -- Lewis acid catalysis -- Enolate alkylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.04.036
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: Image 1