Tummatorn Jumreang, Dudley Gregory B
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
J Am Chem Soc. 2008 Apr 16;130(15):5050-1. doi: 10.1021/ja801018r. Epub 2008 Mar 22.
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.
