Journal of Synthetic Organic Chemistry, Japan. Coupling an irreversible Tishchenko reaction to a reversible aldol reaction overcame the retro-aldol reaction problem and thereby afforded the products in high enantio and diastereoselectivity using 10 mol % of the asymmetric catalyst. rac 2.10 The Aldol Reaction: Transition Metal Enolate. Palladium-Catalyzed Stereoselective Cyclization of 10.1002/1521-3757(20011015)113:20<3995::AID-ANGE3995>3.0.CO;2-D. 10.1002/1521-3773(20011015)40:20<3877::AID-ANIE3877>3.0.CO;2-S,<601::AID-ANIE601>3.0.CO;2-W, http://www.wiley‐ Fieser and Fieser's Reagents for Organic Synthesis. Supporting information for this article is available on the WWW under http://www.wiley‐ or from the author. Catalytic Enantioselective Aldol Addition Reactions. Mixed Imidazolin-2-iminato–Cp* Thorium(IV) Complexes: Synthesis and Reactivity Toward Oxygen-Containing Substrates. Convergent and flexible approach to stereodefined polyhydroxylated fragments. Cationic rare-earth metal SALEN complexes. Construction of quaternary carbon centers by a base-catalyzed enantioselective aldol reaction and related reactions of trimethoxysilyl enol ethers. . Synthesis and structural characterization of scandium SALEN complexes. Zeitschrift f�r anorganische und allgemeine Chemie. and you may need to create a new Wiley Online Library account. . . Any queries (other than missing content) should be directed to the corresponding author for the article. Catalytic Diastereoselective Reductive Claisen Rearrangement. ChemInform Abstract: First Catalytic Asymmetric Aldol‐Tishchenko Reaction — Insight into the Catalyst Structure and Reaction Mechanism.. -Lactide Polymerization Support from Amoco Chemicals is also appreciated. Enantioselective Desymmetrization of meso‐Aziridines with TMSN3 or TMSCN Catalyzed by Discrete Yttrium Complexes. Catalytic Transformation of Aldehydes with Nickel Complexes through η Synthesis, structure and reactivity of samarium complexes supported by Schiff-base ligands. The Tishchenko reaction refers to the dimerization of an aldehyde in the presence of a metal catalyst to form an ester. Dynamic Structural Change of the Self‐Assembled Lanthanum Complex Induced by Lithium Triflate for Direct Catalytic Asymmetric Aldol–Tishchenko Reaction. Coordination and Oxidative Cyclization A Novel Utilization of Acylsilanes in Organic Synthesis. 3 Acid-catalyzed aldol-Meerwein–Ponndorf–Verley-etherification reactions—access to defined configured quaternary stereogenic centers. Synthesis, reactivity and structural characterization of ytterbium complexes bearing a tridentate [O,N,N] Schiff base ligand. Rapid assembly of anti-1,3-diol units with 2-quaternary carbon stereocenter via samarium diiodide-promoted tandem Aldol/Evans-Tishchenko reaction. stereogenic center New Cyclotrimerization of Aldehydes to Cyclopentenone or Tetrahydrofuran Induced by Dibromotriphenylphosphorane. . Direct asymmetric aldol-Tishchenko reaction of aliphatic ketones catalyzed by syn-aminoalcohol–Yb(iii) complexes. The Tishchenko Reaction is a disproportionation reaction that allows the preparation of esters from two equivalents of an aldehyde. Enantioselective Direct Aldol-Tishchenko Reaction:  Access to Chiral Stereopentads. Enantioselective cyanosilylation of ketones catalyzed by double-activation catalysts with N-oxides. The Zirconium Alkoxide‐Catalyzed Aldol‐Tishchenko Reaction of Ketone Aldols. Ad=adamantyl. Selective Crossed‐Tishchenko Reaction—A Waste‐Free Synthesis of Benzyl Esters. Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction. The first example of a catalytic asymmetric aldol-Tishchenko reaction of aldehydes and aliphatic ketones. Learn about our remote access options, Department of Chemistry Venable and Kenan Laboratories The University of North Carolina Chapel Hill, NC 27599‐3290, USA, Fax: (+1) 919‐962‐2388. Enantioselective Cyanosilylation of Ketones by a Catalytic Double‐Activation Method with an Aluminium Complex and an N‐Oxide. Catalytic enantioselective aldol reactions. Metal–Salen Schiff base complexes in catalysis: practical aspects. Synthesis and Characterization of Yttrium and Ytterbium Complexes Supported by Salen Ligands and Their Catalytic Properties for 2 A direct catalytic asymmetric aldol reaction of propionate equivalent was achieved via the aldol-Tishchenko reaction. La Complex@Fe–PILM Offering Resilient Option for Efficient and Green Processing toward Epoxidation of Cyclohexene. Direct Asymmetric Aldol‐Tishchenko Reaction. (1)]. Mechanism of the Tishchenko Reaction The aluminium alkoxide acts as a Lewis acid to coordinate with one molecule of the aldehyde, and to facilitate the addition of a second equivalent of aldehyde, generating a hemiacetal intermediate: Carbohydrate-Derived Amino-Alcohol Ligands for Asymmetric Alkynylation of Aldehydes. Lanthanide alkoxide complexes stabilized by a novel salen-type Schiff-base ligand: Synthesis, structure, and catalysis for the polymerization of lactide. 4) A modification of the Tishchenko reaction is the aldol-Tishchenko reaction where the aldehyde first undergoes an aldol reaction followed by the Tishchenko reaction to Journal of the American Chemical Society. • The Tishchenko reaction of acetaldehyde gives the commercially important solvent ethyl acetate. Chiral salen ligands designed to form polymetallic complexes. Tandem aldol-transfer–Tischtschenko reaction of aldehydes and β-hydroxyketones catalyzed by trimethylaluminum. Synthesis, Crystal Structure, Fluorescent and Antioxidation Properties of Cerium(III) and Europium(III) Complexes with Bis(3‐methoxysalicylidene)‐3‐oxapentane‐1,5‐diamine. Enantioenriched Bifunctional Crotylsilanes for the Asymmetric Synthesis of Orthogonally Protected 2-Methyl-1,3-diols. Number of times cited according to CrossRef: Recent Advances and Prospects in the Tishchenko Reaction. Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones. J.P.M. Chiral Ytterbium Complex‐Catalyzed Direct Asymmetric Aldol‐Tishchenko Reaction: Synthesis of anti‐1,3‐Diols. The catalyst was developed through the combination of arrayed catalyst … Catalytic asymmetric synthesis of enantioenriched β-nitronitrile bearing a C-CF Variants of the Tishchenko reaction include the aldol-Tishchenko reaction, in which an aldol reaction precedes a Tishchenko process, and the Evans-Tishchenko reaction, in which samarium diiodide and an aldehyde are used to convert β-hydroxy ketones to anti -1,3-diol monoesters. The catalytic aldol– Tishchenko reaction, by which an enolizable aldehyde or ketone 92 undergoes coupling with 2 equivalents of aldehydes 91 with a full atom economy to afford 1,3-diol monoesters 93, is an attractive alternative to the direct aldol reaction (Scheme 33). Tishchenko reaction of aldehydes in the presence of an amino alcohol-based Ir bifunctional catalyst was developed. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use. Unmodified carbonyl compounds are converted in an enantioselective aldol‐Tishchenko reaction directly into the chiral adduct by using catalytic amounts of a chiral base prepared in situ [Eq. The full text of this article hosted at is unavailable due to technical difficulties. The authors thank Prof. Joseph Templeton for helpful discussions and Andrew Larsen of the Gagné research group for assistance with vapor pressure osmometry experiments. The catalyst was developed through the combination of arrayed catalyst evaluation and informed ligand design. Enantioselective Evans-Tishchenko Reduction of b-Hydroxyketone Catalyzed by Lithium Binaphtholate. An effect of the ionic radii of lanthanide(III) ions on the structure and catalytic properties of chiral Schiff base-lanthanide(III) complexes. Zirconium–BINOLate-catalyzed, enantioselective aldol-Tishchenko reactions of aromatic ketone aldols. Stereoselective Synthesis of 2-Fluoro-1,3-Diols via Lithium Binaphtholate-Catalyzed Aldol–Tishchenko Reaction. Zeitschrift für anorganische und allgemeine Chemie. in Situ Double Catalytic Kinetic Resolution (DoCKR) of Acyclic anti‐1,3‐Diols: The Additive Horeau Amplification. Bimetallic catalysis in the highly enantioselective ring–opening reactions of aziridines. Progressive Studies on the Novel Samarium‐Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondary α‐Hydroxy Epoxides.

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