Exploring Morita-Baylis-Hillman reactions of p-quinols.

Org Lett

Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, C/Francisco Tomás y Valiente 7, Cantoblanco, 28049-Madrid, Spain.

Published: February 2010

The Morita-Baylis-Hillman reaction of p-methylquinols with activated aromatic aldehydes has been studied. Depending on the reaction conditions (solvent and additives), three different products were formed. A mono or double Morita-Baylis-Hillman adduct and a fused 1,3-dioxolane could be obtained in good chemical yields. The use of non-nucleophilic bases to promote the reaction suggested an autocatalytic mechanism.

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Source
http://dx.doi.org/10.1021/ol902763gDOI Listing

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