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.
Tummatorn
Jumreang
J
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
Dudley
Gregory B
GB
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry*
D000480:Alkynes; D020005:Propanols; D011753:Pyrones; D006859:Hydrogen; C028255:propargyl alcohol