Diastereomerically pure rarely functionalized alkenoyl dihydropyrans, 1,6-diketones, and cyclopentanes from acetylene gas and ketones†,10.1039/D2OB01068B

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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 Pub Date : 07/27/2022 00:00:00 , DOI:10.1039/D2OB01068B

Abstract

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.