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Michael addition (conjugate addition)

7 real reactions from the literature, on α,β-unsaturated esters, α,β-unsaturated ketones and malonate esters. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Michael addition: dimethyl malonate (a malonate ester) and acrolein (an α,β-unsaturated aldehyde) with NaOMe, MeOH gives dimethyl 2-(2-oxoethyl)malonate (the 1,5-dicarbonyl (Michael adduct)). 58% yield.
    Michael additionJ. Am. Chem. Soc. 1979, 101, 7032

  2. Michael addition: an α,β-unsaturated ester with CH3NO2, DBU, RT 1 h gives the 1,5-dicarbonyl (Michael adduct).
    Michael addition10.1021/acs.orglett.8b01259

  3. Michael addition: an α,β-unsaturated ester with 1,3-cyclopentanedione, DCE, 80 C, 3 d gives the 1,5-dicarbonyl (Michael adduct).
    Michael addition10.1021/acs.orglett.8b01259

  4. Michael addition: phenylacetonitrile and methyl acrylate (an α,β-unsaturated ester) with 2 eq; tBuOK gives methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate (the 1,5-dicarbonyl (Michael adduct)).
    Michael additionRealOChem worksheet

  5. Michael addition: chalcone (an α,β-unsaturated ketone) with KCN, AcOH; CH3CH2OH, H2O gives gamma-oxo-alpha-phenylbenzenebutanenitrile (the 1,5-dicarbonyl (Michael adduct)).
    Michael additionOrg. Synth. Coll. Vol. 2, p. 498

  6. Michael addition: 2-isopropyl-5-methylcyclopentanone (a five-membered cyclic ketone) and 1-methoxy-3-buten-2-one (an α,β-unsaturated ketone) with KOEt, EtOH gives the 1,5-dicarbonyl (Michael adduct).
    Michael additionJ. Org. Chem. 1973, 38, 3663

  7. Michael addition: an α,β-unsaturated ketone with 1); Me2CuLi; Et2O; 2) H+ gives (5R)-2,3-dimethyl-5-prop-1-en-2-ylcyclohexan-1-one (the 1,5-dicarbonyl (Michael adduct)).
    Michael additionRealOChem worksheet