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Robinson Annulation

Michael Addition

The 1,4-addition (or conjugate addition) of resonance-stabilized carbanions. The Michael Addition is thermodynamically controlled; the reaction donors are active methylenes such as malonates and nitroalkanes, and the acceptors are activated olefins such as α,β-unsaturated carbonyl compounds.

Examples:

donors

acceptors


Mechanism of the Michael Addition

Recent Literature


Ionic Liquid as Catalyst and Reaction Medium. The Dramatic Influence of a Task-Specific Ionic Liquid, [bmIm]OH, in Michael Addition of Active Methylene Compounds to Conjugated Ketones, Carboxylic Esters, and Nitriles
B. C. Ranu, S. Banerjee, Org. Lett., 2005, 7, 3049-3052.


Diphenylprolinol Methyl Ether: A Highly Enantioselective Catalyst for Michael Addition of Aldehydes to Simple Enones
Y. Chi, S. H. Gellman, Org. Lett., 2005, 7, 4253-4256.


Consecutive Michael-Claisen Process for Cyclohexane-1,3-dione Derivative (CDD) Synthesis from Unsubstituted and Substituted Acetone
D. Sharma, Bandna, A. K. Shil, B. Singh, P. Das, Synlett, 2012, 23, 1199-1204.


Construction of Quaternary Stereocenters by Efficient and Practical Conjugate Additions to α,β-Unsaturated Ketones with a Chiral Organic Catalyst
F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. Int. Ed., 2006, 45, 947-950.


P-BEMP: A New Efficient and Commercially Available User-Friendly and Recyclable Heterogeneous Organocatalyst for the Michael Addition of 1,3-Dicarbonyl Compounds
D. Bensa, T. Constantieux, J. Rodriguez, Synthesis, 2004, 923-927.


An asymmetric direct Michael addition of α,β-unsaturated aldehydes with acetophenone catalyzed by a Jřrgensen-Hayashi catalyst in methanol gave δ-keto aldehydes in up to 82% yield and 98% ee.
W. Li, W. Wu, J. Yang, X. Liang, J. Ye, Synthesis, 2011, 1085-1091.


A new reactivity pattern for vinyl bromides: cine-substitution via palladium catalysed C-N coupling/Michael addition reactions
M. C. Willis, J. Chauhan, W. G. Whittinham, Org. Biomol. Chem., 2005, 3, 3094-3095.


Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Simple trans-4-Hydroxyprolylamide
C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. Int. Ed., 2006, 45, 5984-5987.


Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea
T. Okino, Y. Hoashi, T. Fukukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc., 2005, 7, 119-125.


A Novel Recyclable Organocatalytic System for the Highly Asymmetric Michael Addition of Aldehydes to Nitroolefins in Water
D. Sarkar, R. Bhattarai, A. D. Headley, B. Ni, Synthesis, 2011, 1993-1997.


Importance of Chiral Phase-Transfer Catalysts with Dual Functions in Obtaining High Enantioselectivity in the Michael Reaction of Malonates and Chalcone Derivatives
T. Ooi, D. Ohara, K. Fukumoto, K. Maruoka, Org. Lett., 2005, 7, 3195-3197.


Highly Efficient C-C Bond-Forming Reactions in Aqueous Media Catalyzed by Monomeric Vanadate Species in an Apatite Framework
T. Hara, S. Kanai, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, J. Org. Chem., 2006, 71, 7455-7462.


Expanding the Scope of Lewis Acid Catalysis in Water: Remarkable Ligand Acceleration of Aqueous Ytterbium Triflate Catalyzed Michael Addition Reactions
R. Ding, K. Katebzadeh, L. Roman, K.-E. Bergquist, U. M. Lindström, J. Org. Chem., 2006, 71, 352-355.


Reconstructed Hydrotalcite as a Highly Active Heterogeneous Base Catalyst for Carbon-Carbon Bond Formations in the Presence of Water
K. Ebitani, K. Motokura, K. Mori, T. Mizugaki, K. Kaneda, J. Org. Chem., 2006, 71, 5440-5447.


DABCO-Based Ionic Liquids: Recyclable Catalysts for Aza-Michael Addition of α,β-Unsaturated Amides under Solvent-Free Conditions
A. Ying, Z. Li, J. Yang, S. Liu, S. Xu, H. Yan, C. Wu, J. Org. Chem., 2014, 79, 6510-6516.


Silicon Tetrachloride Catalyzed Aza-Michael Addition of Amines to Conjugated Alkenes under Solvent-Free Conditions
N. Azizi, R. Baghi, H. Ghafuri, M. Boloutchian, M. Hashemi, Synlett, 2010, 379-382.


Cellulose-Supported Copper(0) Catalyst for Aza-Michael Addition
K. R. Reddy, N. S. Kumar, Synlett, 2006, 2246-2250.


Ceric Ammonium Nitrate Catalyzed aza-Michael Addition of Aliphatic Amines to α,β-Unsaturated Carbonyl Compounds and Nitriles in Water
R. Varala, N. Sreelatha, S. R. Adapa, Synlett, 2006, 1549-1553.


Ethyl Glyoxylate N-Tosylhydrazone as Sulfonyl-Transfer Reagent in Base-Catalyzed Sulfa-Michael Reactions
M. Fernández, U. Uria, L. Orbe, J. L. Vicario, E. Reyes, L. Carrillo, J. Org. Chem., 2014, 79, 230-239.


Construction of 5,6-Ring-Fused 2-Pyridones: An Effective Annulation Tactic Achieved in Water
A. B. Smith, III, O. Atasoylu, D. C. Beshore, Synlett, 2009, 2643-2646.


Organic Chemistry Highlights
Michael Reactions for Enantioselective Ring Construction
Enantioselective Aza-Henry and Aza-Michael Reactions