76641-71-9Relevant articles and documents
Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones
Vil, Vera A.,Gomes, Gabriel Dos Passos,Ekimova, Maria V.,Lyssenko, Konstantin A.,Syroeshkin, Mikhail A.,Nikishin, Gennady I.,Alabugin, Igor V.,Terent'Ev, Alexander O.
, p. 13427 - 13445 (2018/11/02)
We have discovered synthetic access to β-hydroperoxy-β-peroxylactones via BF3-catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals, with H2O2. Strikingly, independent of the choice of starting material, these reactions converge at the same β-hydroperoxy-β-peroxylactone products, i.e., the peroxy analogues of the previously elusive cyclic Criegee intermediate of the Baeyer-Villiger reaction. Computed thermodynamic parameters for the formation of the β-hydroperoxy-β-peroxylactones from silyl enol ethers, enol acetates, and cyclic acetals confirm that the β-peroxylactones indeed correspond to a deep energy minimum that connects a variety of the interconverting oxygen-rich species at this combined potential energy surface. The target β-hydroperoxy-β-peroxylactones were synthesized from β-ketoesters, and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals were obtained in 30-96% yields. These reactions proceed under mild conditions and open synthetic access to a broad selection of β-hydroperoxy-β-peroxylactones that are formed selectively even in those cases when alternative oxidation pathways can be expected. These β-peroxylactones are stable and can be useful for further synthetic transformations.
Efficient synthesis of α-(hydroxymethyl) ketones not available through aldol-type processes
Hitchcock,Perron,Martin,Albizati
, p. 1059 - 1061 (2007/10/02)
An efficient synthesis of α-(hydroxymethyl) ketones from β-keto esters has been developed, which is experimentally simple, amenable to large scale production and provides products of high purity without resort to chromatography in most cases. The method is a useful alternative and complement to condensation processes.
Synthesis and pharmacological test of 2-and 3-substituted pyrano[2,3-b]indolones (author's transl)
Bartsch,Eiden,Buchborn
, p. 481 - 490 (2007/10/02)
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