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Mukaiyama Aldol Addition

Lianyungang Klinechem Co.,Ltd | Updated: Dec 12, 2018

Mukaiyama Aldol Addition

The use of silyl enol ethers as an enolate equivalent in Lewis acid-catalyzed aldol additions. The trimethylsilyl group is thought of as a sterically demanding hydrogen equivalent that activates the enol and traps the aldol hydroxyl.

Mechanism of the Mukaiyama Aldol Addition

The open transition state is preferred, but the outcome of the reaction (syn/anti) depends on the size of substituents and on the Lewis acid. New modified protocols allow syn- or anti-selective transformations and even the selective preparation of enantiomers.

Transition-state for syn-selective transformations:

Recent Literature

BINAP/AgOTf/KF/18-Crown-6 as New Bifunctional Catalysts for Asymmetric Sakurai-Hosomi Allylation and Mukaiyama Aldol Reaction
M. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem.200368, 5593-5601.

Bismuth Triflate-Chiral Bipyridine Complexes as Water-Compatible Chiral Lewis Acids
S. Kobayashi, T. Ogino, H. Shimizu, S. Ishikawa, T. Hamada, K. Manabe, Org. Lett.20057, 4729-4731.

P(PhCH2NCH2CH2)3N Catalysis of Mukaiyama Aldol Reactions of Aliphatic, Aromatic, and Heterocyclic Aldehydes and Trifluoromethyl Phenyl Ketone
V. R. Chintareddy, K. Wadhwa, J. G. Verkade, J. Org. Chem.200974, 8118-8132.

Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate
C. W. Downey, M. W. Johnson, D. H. Lawrence, A. S. Fleisher, K. J. Tracy, J. Org. Chem.201075, 5351-5354.

Aluminum Bis(trifluoromethylsulfonyl)amides: New Highly Efficient and Remarkably Versatile Catalysts for C - C Bond Formation Reactions
A. Marx, H. Yamamoto, Angew. Chem. Int. Ed.200039, 178-181.

One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf
C. W. Downey, M. W. Johnson, K. J. Tracy, J. Org. Chem.200873, 3299-3302.

Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes
Y. Inamoto, Y. Nishimoto, M. Yasuda, A. Baba, Org. Lett.201214, 1168-1171.

Strong Counteranion Effects on the Catalytic Activity of Cationic Silicon Lewis Acids in Mukaiyama Aldol and Diels-Alder Reactions
L.-B. Han, C.-Q. Zhao, J. Org. Chem.200570, 10121-10123.

A Polymer-Supported Phosphoramide as a Lewis-Base Catalyst for the Catalytic Aldol Reaction
R. A. Flowers II, X. Xu, C. Timmons, G. Li, Eur. J. Org. Chem.2004, 2988-2990.

Catalysis of Mukaiyama Aldol Reactions by a Tricyclic Aluminum Alkoxide Lewis Acid
S. M. Raders, J. G. Verkade, J. Org. Chem.200974, 5417-5428.

N-Heterocyclic Carbene-Catalyzed Mukaiyama Aldol Reactions
J. J. Song, Z. Tan, J. T. Reeves, N. K. Yee, C. H. Senanayake, Org. Lett.20079, 1013-1016.

Sodium Phenoxide-Phosphine Oxides as Extremely Active Lewis Base Catalysts for the Mukaiyama Aldol Reaction with Ketones
M. Hatano, E. Takagi, K. Ishihara, Org. Lett.20079, 4527-4530.

Lewis Base Activation of Lewis Acids: Catalytic, Enantioselective Addition of Silyl Ketene Acetals to Aldehydes
S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc.2005127, 3774-3789.

Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-Derived Silicon Enolate with Aldehydes: An Efficient Approach to the Asymmetric Synthesis of anti-β-Hydroxy-α-Amino Acid Derivatives
J. Kobayashi, M. Nakamura, Y. Mori, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc.2004126, 9192-9193.

C1-Symmetric Sulfoximines as Ligands in Copper-Catalyzed Asymmetric Mukaiyama-Type Aldol Reactions
M. Langner, C. Bolm, Angew. Chem. Int. Ed., 200443, 5984-5987.

Lewis Base Activation of Lewis Acids. Vinylogous Aldol Addition Reactions of Conjugated N,O-Silyl Ketene Acetals to Aldehydes
S. E. Denmark, J. R. Heemstra, Jr., J. Am. Chem. Soc.2006128, 1038-1039.

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