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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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https://hal-normandie-univ.archives-ouvertes.fr/hal-03200519
Contributor : Jean-François Brière <>
Submitted on : Friday, April 16, 2021 - 4:01:32 PM
Last modification on : Sunday, April 18, 2021 - 3:24:13 AM

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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, Wiley-VCH Verlag, In press, ⟨10.1002/anie.202014489⟩. ⟨hal-03200519⟩

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