Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones. (6th April 2021)

• Record Type: Journal Article
• Authors: Wittmann, Stéphane; Martzel, Thomas; Pham Truong, Cong Thanh; Toffano, Martial; Oudeyer, Sylvain; Guillot, Régis; Bournaud, Chloée; Gandon, Vincent; Brière, Jean‐François; Vo‐Thanh, Giang
• Is Part Of: Angewandte Chemie. Volume 133:Number 20(2021)
• Page Start: 11210
• Page End: 11214
• Publication Date: 2021-04-06
• Subjects: asymmetric synthesis -- dihydropyranones -- Meldrum's acid -- organocatalysis -- vinylogy; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202014489
• Languages: English
• ISSNs: 0044-8249

Abstract

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, providing an unprecedented route to 3, 6‐dihydropyran‐2‐ones 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. Abstract : Disubstituted alkylidene Meldrum's acids proved to be novel C4‐synthons capable of undergoing a vinylogous formal (4+2) cycloaddition reaction with reactive ketones, providing an unprecedented route to chiral 3, 6‐dihydropyran‐2‐ones under Brønsted base organocatalytic conditions.