Journal of the American Chemical Society, Vol.130, No.15, 5050-5050, 2008
Ring opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols
Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.