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Lewis acid catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates.

ABSTRACT: Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH(3)CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.

SUBMITTER: Tran V

PROVIDER: S-EPMC3518682 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Lewis acid catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates.

Tran Vincent V Minehan Thomas G TG

Organic letters 20121121 23

Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH(3)CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis. ...[more]

PMID: 23170869

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