Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones - Normandie Université Access content directly
Journal Articles Angewandte Chemie International Edition Year : 2021

Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones

Abstract

Upon Brønsted base organocatalysis, ketone derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able to undergo a formal (4+2) cycloaddition reaction with dihydro-2,3-furandione to furnish an unprecedented route to 3,6dihydropyran-2-ones 5 as spiro[4,5]decane derivatives with up to 98% ee thanks to the commercially available Takemoto catalyst. Preliminary investigation showed that this reaction could be extended to other activated ketones establishing these alkylidene Meldrum's acids as a novel C4-synthon in the vinylogous series.
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Dates and versions

hal-03200519 , version 1 (16-04-2021)

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Stéphane Wittmann, Thomas Martzel, Cong Thanh Pham Truong, Martial Toffano, Sylvain Oudeyer, et al.. Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones. Angewandte Chemie International Edition, 2021, 60, pp.11110-11114. ⟨10.1002/anie.202014489⟩. ⟨hal-03200519⟩
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