Michael Addition of Allenoates to Electron-Deficient Olefins: Facile Synthesis of 2-Alkynyl-Substituted Glutaric Acid Derivatives.

[摘要]：A Michael addn. of allenoates R1CH:C:C(Me)CO2Et (R1 = Me, Me2CH, n-hexyl, Ph, 4-MeOC6H4, PhCH2, etc.) to electron-deficient olefins was mediated efficiently by a catalytic amt. of com. tetra-n-butylammonium fluoride under mild conditions. The corresponding 2-alkynyl-substituted glutaric acid derivs. R1CYCCMe(CO2Et)CHR2CHR3X, which may be potential building blocks in org. synthesis, were obtained in good to excellent yields from these reactions. The mechanism for the Michael addn. reaction may involve the formation of an alkynylenolate intermediate.

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