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  • Title: Zirconium-promoted epoxide rearrangement-alkynylation sequence.
    Author: Albert BJ, Koide K.
    Journal: J Org Chem; 2008 Feb 01; 73(3):1093-8. PubMed ID: 18179236.
    Abstract:
    Additions of terminal alkynes to electrophiles are important transformations in organic chemistry. Generally, activated terminal alkynes react with epoxides in an S(N)2 fashion to form homopropargylic alcohols. We have developed a new synthetic method to form propargylic alcohols from epoxides and terminal alkynes via 1,2-shifts. This method involves cationic zirconium acetylides as both the activator of epoxides and nucleophiles. Due to the mild conditions to pre-activate alkynes with silver nitrate, this synthetic method is useful for both electron-rich and electron-deficient alkynes with other acid- and base-sensitive functional groups.
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