Ring opening reactions of 2-methyleneoxetanes

Ring opening of 2-methyleneoxetanes with stabilized carbanion nucleophiles provides substituted ketones. The intermediate enolate can be trapped as its silylenol ether. If the 2-methyleneoxetane is exposed to more strongly basic carbanions, the corresponding homopropargylic alcohol is isolated in excellent yield. A variety of heteroatom nucleophiles also open the 2-methyleneoxetane in good to excellent yields.