A Brønsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane.

ABSTRACT

MeSO3H effects the intramolecular allenylation of a series of aldehydes 1 to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78 degrees C. However, when the reaction is performed at room temperature, aldehyde 1 provides enone product 7 instead. A mechanism for the formation of this product is proposed in which the initially formed allenyl alcohol 3 undergoes dehydration to provide an allyl carbocation, which is trapped with water, thereby installing the enone.