Synthesis and Carbodemetalation Reactions of 4-Methyl- and 5-Aryl-2-(trimethylsilyl)oxazoles. C-C Bond Formation at C2 of the Oxazole Ring
The title compounds 6a-d have been prepared by sequential lithiation and silylation of the corresponding 2-H oxazoles and isomerization of the resulting α-isocyano silyl enol ethers.Silyloxazoles 6a-d behave as stable 2-oxazolyl anion equivalents toward v
Intramolecular Insertion of the Isonitrile Group into an Oxygen-Silicon Bond. Synthesis of a 2-Trimethylsilyloxazole via the α-Isocyano Silyl Enol Ether
Treatment of lithiated 4-methyloxazole (1b) with trimethylsilyl chloride gives the α-isocyano silyl enol ether (4b) which when heated in the presence of potassium hydroxide undergoes ring closure to the 2-trimethylsilyloxazole (5b) whose reactions with C-