Diastereomerically pure rarely functionalized alkenoyl dihydropyrans, 1,6-diketones, and cyclopentanes from acetylene gas and ketones.

Inna V Tatarinova, Natal'ya A Lobanova, Igor' A Ushakov, Elena Yu Schmidt, Boris A Trofimov

Organic & biomolecular chemistry 2022 Aug 24

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Pure (E)-alkenoyl dihydropyrans are stereoselectively assembled from 2-acetyl-3,4-dihydropyrans (products of one-pot self-organization of acetylene gas and ketones) and aromatic aldehydes (52-86% yields). Furthermore, (E)-alkenoyl dihydropyrans undergo ring opening (acid hydrolysis) to afford 5-hydroxy-1,6-diketones (44-67% yields) and acetyl-2-(E)-styryl-2,3-dihydroxycyclopentanes (19-32% yields), both as single diastereomers.

Citation

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. Organic & biomolecular chemistry. 2022 Aug 24;20(33):6593-6605