Sequential Michael addition/retro-Claisen condensation of aromatic β-diketones with α,β-unsaturated esters: an approach to obtain 1,5-ketoesters?
Organic & Biomolecular Chemistry Pub Date: 2016-01-21 DOI: 10.1039/C5OB02570B
Abstract
A K2CO3-catalyzed one-pot protocol involving sequential C–C bond formation and cleavage of aromatic β-diketones with α,β-unsaturated esters is developed to obtain 1,5-ketoesters. The sequential reaction via Michael addition and retro-Claisen condensation proceeds smoothly under mild conditions in up to 98% isolated yield. The mechanism study disclosed that the cascade process involved C–C bond cleavage of aromatic β-diketone as a phenacyl donor under alcoholic alkalescent conditions.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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