Michael 4 Base Dazzling
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Further Information
Literature
Related Reactions
Robinson Annulation
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.
Direct Synthesis of β-Aminoketones from Amides via Novel Sequential Nucleophilic Substitution/Michael Reaction
A. Gomtsyan, Org. Lett., 2000, 2, 11-13.
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 Jørgensen-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.
Helical peptide foldamers catalyze Michael addition reactions of nitroalkanes or dialkyl malonates to α,β-unsaturated ketones to give Michael adducts with high enantioselectivities. The amide protons at the N terminus in the α-helical peptide catalyst are crucial for activating Michael donors, while the N-terminal primary amine activates Michael acceptors through the formation of iminium ion intermediates.
A. Ueda, T. Umeno, M. Doi, K. Akagawa, K. Kudo, M. Tanaka, J. Org. Chem., 2016, 81, 6343-6356.
Highly Enantioselective Michael Addition of Nitroalkanes to Enones and Its Application in Syntheses of (R)-Baclofen and (R)-Phenibut
X.-T. Guo, J. Shen, F. Sha, X.-Y. Wu, Synthesis, 2015, 47, 2063-2072.
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.
Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins
S. Kim, S. Kang, G. Kim, Y. Lee, J. Org. Chem., 2016, 81, 4048-4057.
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.
A Michael Addition-Asymmetric Transfer Hydrogenation One-Pot Enantioselective Tandem Process for Syntheses of Chiral γ-Secondary Amino Alcohols
L. Wu, R. Jin, L. Li, X. Hu, T. Cheng, G. Liu, Org. Lett., 2017, 19, 3047-3050.
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.
Michael Reactions for Enantioselective Ring Construction
Enantioselective Aza-Henry and Aza-Michael Reactions
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