Coupling of alkynyl organometallics with 4-acetoxy-1,3-dioxanes: Synthesis of propargylic and allylic anti-1,3-diols

Article abstract of DOI:10.1016/S0040-4039(98)00512-7

Alkynyl diethylalanes and stannanes couple with 4-acetoxy-1,3-dioxane 1 in the presence of BF₃ · OEt₂ to give acetal protected propargylic anti- 1,3-diols 2 in high yield, with exquisite diastereoselectivity and little acetal epimerization. These propargylic dioxanes 2 are useful intermediates for further diastereoselective reactions.