Categories: C-C Bond Formation > Oxygen-containing molecules > Alcohols >
Synthesis of homoallylic alcohols
In the presence of a cobalt catalyst, the reaction of epoxides with dimethylsulfoxonium methylide delivers homoallylic alcohols instead of oxetanes. The observed reactivity change appears to be specifically due to cobalt salts and is broadly applicable to a variety of epoxides, retaining the initial stereochemistry.
M. L. Jamieson, P. A. Hume, D. P. Furkert, M. A. Brimble, Org. Lett., 2016, 18, 468-471.
Formaldehyde Encapsulated in Zeolite: A Long-Lived, Highly Activated One-Carbon Electrophile to Carbonyl-Ene Reactions
T. Okachi, M. Onaka, J. Am. Chem. Soc., 2004, 126, 2306-2307.