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Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of ?-, ?- and ?-lactones.

ABSTRACT: Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted ?-, ?-, and ?-lactones in good to excellent yields.

SUBMITTER: Christopher A

PROVIDER: S-EPMC3845887 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.

Christopher Aaron A Brandes Dahniel D Kelly Stephen S Minehan Thomas G TG

Organic & biomolecular chemistry 20131010 44

Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted β-, γ-, and δ-lactones in good to excellent yields. ...[more]

PMID: 24114116

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