Synthesis and Utility of 2,2-Dimethyl-2 H-pyrans: Dienes for Sequential Diels-Alder/Retro-Diels-Alder Reactions.

Org Lett

Instituto de Productos Naturales y Agrobiología , Consejo Superior de Investigaciones Científicas , Avda. Astrofísico Francisco Sánchez 3 , 38206 La Laguna , Canary Islands , Spain.

Published: December 2018

The practical use of 2,2-dimethyl-2 H-pyrans as electron-rich dienes in sequential Diels-Alder/retro-Diels-Alder (DA/rDA) domino processes to generate aromatic platforms has been demonstrated. Different polysubstituted alkyl 2-naphthoates have been synthesized by the DA/rDA reaction of benzynes and 2,2-dimethyl-2 H-pyrans. The use of other activated alkynes allows the access of substituted alkyl benzoate derivatives.

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http://dx.doi.org/10.1021/acs.orglett.8b03558DOI Listing

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