Product‐Catalyzed Aldol Reaction between Trimethylsilyl Enolates and Aldehydes
Advanced Synthesis & CatalysisPublished 1 August 2004
Hidehiko Fujisawa, Takashi Nakagawa, Teruaki Mukaiyama
Citations49
SJR quartileQ1
SJR score0.93
SNIP0.92
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
Abstract Aldol reactions between trimethylsilyl ketene acetals and aldehydes by using a catalytic amount of alkoxide anion proceeded smoothly to afford the corresponding aldols in DMF, indicating that the initially‐formed aldolate anion effectively worked to catalyze the reaction. The “product‐catalyzed aldol reaction”, a new class Lewis base‐catalyzed aldol reaction, between trimethylsilyl ketene acetals and aldehydes was performed successfully by the use of aldolate anion as a Lewis base catalyst.
Keywords
Chemistry
Angewandte Chemie International EditionThe Catalytic Asymmetric Aldol Reaction
858 Citations2000Timothy Machajewski, Chi‐Huey Wong
Two different approaches have been taken toward the catalytic asymmetric aldol reaction: biocatalysis and catalysis with small molecules, which have specific advantages and limitations, and as a result are complementary to each other.
Journal of the American Chemical SocietyNew cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride
796 Citations1974Teruaki Mukaiyama, Kazuo Banno +1 more
Chemical ReviewsDiastereoselection in Lewis-Acid-Mediated Aldol Additions
447 Citations1999Rainer Mahrwald
The evolution of stereoselective Lewis-acid-mediated aldol-type addition up to the recent development of chiral Lewis acids is covered, which gives the main advantages in the Mukaiyama approach are the chemoselectivity of the reaction and the possibility of stereOSElective execution.
Tetrahedron AsymmetryCatalyzed enantioselective aldol additions of latent enolate equivalents
378 Citations1998Scott G. Nelson
Accounts of Chemical ResearchAsymmetric Catalysis of Aldol Reactions with Chiral Lewis Bases
310 Citations2000Scott E. Denmark, Robert A. Stavenger
From a combination of stereochemical, kinetic, and structural studies, an intruiging mechanistic hypothesis is forwarded that explains the origin of catalysis and diastereoselectivity.
Journal of the American Chemical SocietyChemistry of Enoxysilacyclobutanes: Highly Selective Uncatalyzed Aldol Additions
154 Citations1994Scott E. Denmark, Brian D. Griedel +2 more
Journal of the American Chemical SocietyLewis Base-Promoted Aldol Reaction of Dimethylsilyl Enolates in Aqueous Dimethylformamide: Use of Calcium Chloride as a Lewis Base Catalyst
76 Citations2002Katsukiyo Miura, Takahiro Nakagawa +1 more
In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields.
Helvetica Chimica Acta<i>Lewis</i> Base Catalyzed Aldol Reaction of Trimethylsilyl Enolates with Aldehydes
67 Citations2002Teruaki Mukaiyama, Hidehiko Fujisawa +1 more
Chemistry LettersLithium Acetate-Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate
45 Citations2003Takashi Nakagawa, Hidehiko Fujisawa +1 more
Chemistry LettersLewis Base-Catalyzed Mannich-type Reaction between Aldimine and Trimethylsilyl Enolate
43 Citations2003Hidehiko Fujisawa, Eiki Takahashi +2 more
Chemistry LettersLewis Base Catalyzed Michael Reaction between Ketene Silyl Acetals and α,β-Unsaturated Carbonyl Compounds
38 Citations2002Teruaki Mukaiyama, Takashi Nakagawa +1 more
Chemistry LettersLithium Acetate Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate in a Dimethylformamide–H2O Solvent
38 Citations2003Takashi Nakagawa, Hidehiko Fujisawa +1 more
Chemistry LettersA Catalytic Aldol Reaction between Ketene Silyl Acetals and Aldehydes Promoted by Lithium Amide under Non-acidic Conditions
34 Citations2002Hidehiko Fujisawa, Teruaki Mukaiyama
Chemistry LettersLithium Pyrrolidone Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate
29 Citations2002Hidehiko Fujisawa, Teruaki Mukaiyama
Chemistry LettersSelf-promoted Aldol Reaction between Aldehyde Having Lewis Base Moiety and Trimethylsilyl Enolate
28 Citations2003Takashi Nakagawa, Hidehiko Fujisawa +1 more
Chemistry LettersCritical Role of Val567 in Substrate Recognition by Neuronal Nitric Oxide Synthase for NO Formation Activity
2 Citations2003Hiroto Takahashi, Yuko Sato +6 more
Leu and Phe mutations at conserved Val567 located within the substrate binding site of neuronal nitric oxide synthase markedly lowered activity on the physiological substrates, L-Arg and NG-hydroxy-L-Arg, and other potential alkyl- and arylguanidine substrates.
