Michael Addition of Allenoates to Electron-Deficient Olefins: Facile Synthesis of 2-Alkynyl-Substituted Glutaric Acid Derivatives
Реакция Михаэля алленоатов с электроно-дефицитными олефинами: простой синтез производных глутаровой кислоты с 2-алкинильным заместителем
2008-07-25
SCID: 54.1/np8fqdhq
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2-alkynyl-substituted glutaric acid derivativesMichael additionallenoateselectron-deficient olefinstetra-n-butylammonium fluoride (TBAF)
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Abstract (AI)
A Michael addition of allenoates to electron-deficient olefins was mediated efficiently by a catalytic amount of commercial tetra-n-butylammonium fluoride (TBAF) under mild conditions. And 2-alkynyl substituted glutaric acid derivatives, which may be potential building blocks in organic synthesis, were obtained in good to excellent yields from these reactions. The mechanism for the Michael addition reaction may involve the formation of an alkynylenolate intermediate.
Key Findings
1
A catalytic amount of commercial tetra-n-butylammonium fluoride efficiently mediates Michael additions of allenoates to electron-deficient olefins under mild conditions.
2
The proposed reaction mechanism may involve formation of an alkynylenolate intermediate.
3
The reactions provide 2-alkynyl-substituted glutaric acid derivatives in good to excellent yields.
4
The synthesized glutaric acid derivatives may serve as potential building blocks for organic synthesis.
Research Object
2-Alkynyl-substituted glutaric acid derivatives formed by the Michael addition of allenoates to electron-deficient olefins
Research Subject
TBAF-catalyzed Michael addition under mild conditions, including the reaction efficiency, product yields, and possible alkynylenolate-mediated mechanism
Publication Details
Publication Date
2008-07-25
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