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

The Journal of Organic Chemistry
Rui RamalhoLiam R Cox

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.

Citations

Mar 17, 2011·Chemical Communications : Chem Comm·Shichao Yu, Shengming Ma
Feb 22, 2011·Chemical Communications : Chem Comm·Fei ZhaoZhenfeng Xi
Jun 19, 2008·The Journal of Organic Chemistry·Julien BeignetLiam R Cox
Sep 9, 2008·The Journal of Organic Chemistry·Peter J Jervis, Liam R Cox
Aug 21, 2013·The Journal of Organic Chemistry·Zhijia Fang, Martin Wills

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