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

Ramalho, Rui, Jervis, Peter J., Kariuki, Benson, Humphries, Alexander C. and Cox, Liam R. 2008. A Brønsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane. Journal of Organic Chemistry 73 (4) , pp. 1631-1634. 10.1021/jo702351s

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Abstract

MeSO(3)H effects the intramolecular allenylation of a series of aldehydes I 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 04 Jun 2017 03:42
URI: http://orca-mwe.cf.ac.uk/id/eprint/25052

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