Divergent Reactivity of δ-Acetoxy Allenoates with 1,3-Bisnucleo­philes: Synthesis of Multisubstituted Pyran, Dihydropyran, and 3-Vinylpent-2-enedioate Scaffolds

Synthesis DOI: 10.1055/s-0042-1751563 Base-dependent synthesis of tetrasubstituted pyrans or 3,4-dihydropyrans using δ-acetoxy allenoates and enolizable carbonyls like cyclohexan-1,3-dione and ethyl benzoylacetate is reported. Thus, the use of DMAP as an organocatalytic base gives tetrasubstituted pyrans while DBU affords isomeric tetrasubstituted 3,4-dihydropyrans. The reaction of δ-acetoxy allenoates with ethyl benzoylacetate mediated by KO
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Bu furnishes diethyl 3-vinylpent-2-enedioates. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - February 20, 2024 Category: Chemistry Authors: Khan, Shabbir Ahmed Swamy, K. C. Kumara Tags: paper Source Type: research