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Enols and Enolates The Michael Addition Reaction and Conjugate Addition Last updated: May 28th, 2026 | The Michael Addition Reaction (and Conjugate Addition) The Michael reaction ( sometimes Michael Addition ) is the addition of an enolate to an electrophilic alkene, such as an alpha-beta unsaturated ketone, nitrile, or ester The primary driving force is formation of a C-C (single) bond (80 kcal/mol) and breakage of a C-C pi bond (60 kcal/mol) The mechanism for the Michael reaction is 1) deprotonation to form an enolate, 2) conjugate addition of the enolate to the alkene, and 3) protonation of the resulting (new) enolate Conjugate addition (or 1,4-addition) is the generic name for reactions where a nucleophile adds to the beta-carbon of electrophilic alkenes that are in conjugation with an electron-withdrawing group Nucleophiles that can participate in conjugate addition include enolates, amines, thiolates [RS(-)], enamines and dialkylcuprates (Gilman reagents) Grignard reagents do not perform conjugate addition

Given these findings, researchers are now exploring the combination of first-generation MTH1 inhibitors with other therapeutic approaches