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

Stéphane Wittmann (1) , Thomas Martzel (2) , Cong Thanh Pham Truong (1) , Martial Toffano (1) , Sylvain Oudeyer (2) , Régis Guillot (1) , Chloée Bournaud (1) , Vincent Gandon (1, 3) , Jean-François Brière (2) , Giang Vo-Thanh (1)

1 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 LCM - Laboratoire de chimie moléculaire

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.

Mots clés: heterocycle; heterocycle; Meldrum's acid; vinylogous; organocatalysis; asymmetric synthesis

Domaines: Chimie organique; Catalyse

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⟩