Further Information
Literature
Related Reactions
Aldol Addition
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., 2003, 68, 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., 2005, 7, 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., 2009,
74, 8118-8132.
Generation of (E)-Silylketene Acetals in a Rhodium-DuPhos Catalyzed
Two-Step Reductive Aldol Reaction
C.-X. Zhao, J. Bass, J. P. Morken,
Org. Lett., 2001, 3, 2839-2842.
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., 2010,
75, 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., 2000, 39,
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., 2008,
73, 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., 2012,
14, 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., 2005, 70, 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., 2009,
74, 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., 2007,
9, 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., 2007,
9, 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., 2005, 127, 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., 2004, 126, 9192-9193.
C1-Symmetric Sulfoximines as Ligands in
Copper-Catalyzed Asymmetric Mukaiyama-Type Aldol Reactions
M. Langner, C. Bolm, Angew. Chem. Int. Ed., 2004, 43,
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., 2006, 128, 1038-1039.
