Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 May 10;60(20):11110-11114.
doi: 10.1002/anie.202014489. Epub 2021 Apr 6.

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
Affiliations

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

Stéphane Wittmann et al. Angew Chem Int Ed Engl. .

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.

Keywords: Meldrum's acid; asymmetric synthesis; dihydropyranones; organocatalysis; vinylogy.

PubMed Disclaimer

References

    1. R. C. Fuson, Chem. Rev. 1935, 16, 1-27.
    1. For leading reviews on indirect vinylogous catalytic processes, see:
    1. S. E. Denmark, J. R. Heemstra, Jr., G. L. Beutner, Angew. Chem. Int. Ed. 2005, 44, 4682-4698;
    1. Angew. Chem. 2005, 117, 4760-4777;
    1. G. Casiraghi, L. Battistini, C. Curti, G. Rassu, F. Zanardi, Chem. Rev. 2011, 111, 3076-3154.

Publication types