Abstract:
(2R*,4R*)-2-Acetyl-2,6-diaryl-4-methyl-3,4-dihydropyrans (diastereoselectively synthesized from acetylene and ketones in one synthetic operation) undergo ring opening by aqueous NH4Cl (MeCN, 80°C, 8h) to afford diastereomerically pure 5-hydroxy-1,6-diketones in 48–89% yields.
Citation:
E. Yu. Schmidt, N. V. Semenova, I. A. Ushakov, A. V. Vashchenko, B. A. Trofimov, “Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps”, Mendeleev Commun., 29:1 (2019), 17–18
Linking options:
https://www.mathnet.ru/eng/mendc1406
https://www.mathnet.ru/eng/mendc/v29/i1/p17
This publication is cited in the following 3 articles:
Inna V. Tatarinova, Natal'ya A. Lobanova, Igor' A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov, “Diastereomerically pure rarely functionalized alkenoyl dihydropyrans, 1,6-diketones, and cyclopentanes from acetylene gas and ketones”, Org. Biomol. Chem., 20:33 (2022), 6593
E. Yu. Schmidt, B. A. Trofimov, “Acetylene in Organic Synthesis. From the Chaos of Small Molecules to Highly Organized Structures. A Review”, Dokl Chem, 505:1 (2022), 127
Alexander Vashchenko, Vladimir Smirnov, Nadezhda Semenova, Elena Schmidt, “Unusual structure of a biphenyl fragment: the important role of weak interactions”, Acta Crystallogr C Struct Chem, 75:11 (2019), 1454
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