Synthesis of highly functionalized propargylic alcohols:: Direct addition of epoxy acetylides to aldehydes and ketones

Direct nucleophilic addition of terminal alkynes comprising an epoxy group to aldehydes and ketones is reported with BuLi or lithium diisopropylamide for the generation of the corresponding lithium acetylides. This alkynylation reaction tolerates a wide variety of different functional groups (e.g.. alcohols. silyl ethers. halides, double bonds) in the carbonyl compound, as well as in the acetylenic nucleophile, and furnishes highly functionalized propargylic alcohols in good-to-excel lent yields. The method is particularly useful for the regioselective introduction of an epoxide function into multiply unsaturated target molecules.