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

ABSTRACT: We report herein the intramolecular ?-tert-alkylation of unsaturated ?-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.

SUBMITTER: McAtee CC

PROVIDER: S-EPMC6152925 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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

McAtee Christopher C CC Ellinwood Duncan C DC McAtee Rory C RC Schindler Corinna S CS

Tetrahedron 20180421 26

We report herein the intramolecular α-<i>tert</i>-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. ...[more]

PMID: 30262933

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