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… (More)
DOI: 10.1021/jo702351s

Topics

3 Figures and Tables