Functionalized Cyclopentanes via Sc(III)-Catalyzed Intramolecular Enolate Alkylation.

Tetrahedron

University of Michigan, Department of Chemistry, Willard Henry Dow Laboratory, 930 North University Avee, Ann Arbor, MI, 48109, USA.

Published: June 2018

We report herein the intramolecular α--alkylation of unsaturated β-ketoesters which gives rise to highly functionalized cyclopentanes. This strategy 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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152925PMC
http://dx.doi.org/10.1016/j.tet.2018.04.036DOI Listing

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