4.8 Article

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

Journal

ORGANIC LETTERS
Volume 20, Issue 24, Pages 7987-7990

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03558

Keywords

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Funding

  1. Spanish Ministry of Economy and Competitiveness (MINECO)
  2. European Regional Development Funds (ERDF) [CTQ2015-63894-P]
  3. Canarian Agency for Research, Innovation and the Information Society (ACIISI) [2017010019]

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The practical use of 2,2-dimethyl-2H-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-2H-pyrans. The use of other activated alkynes allows the access of substituted alkyl benzoate derivatives.

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