Aldol-Tishchenko reaction
- Aldol-Tishchenko reaction
The Aldol-Tishchenko reaction is a tandem reaction involving an Aldol reaction and a Tishchenko reaction. In organic synthesis it is a method to convert aldehydes and ketones into 1,3-hydroxyl compounds. The reaction sequence in many examples starts from conversion of a ketone into an enolate by action of Lithium diisopropylamide (LDA). The mono-ester diol is then converted into the diol by a hydrolysis step. With both the acetyl trimethylsilane [1] and propiophenone [2] as reactants, the diol is obtained as a pure diastereoisomer.
References
* [1] "Stereoselective Tandem Aldol-Tishchenko Reaction with Acylsilanes" Mitsunori Honda, Ryota Iwamoto, Yoshie Nogami and Masahito Segi Chemistry Letters Vol. 34 (2005) , No. 4 p.466 [http://www.jstage.jst.go.jp/article/cl/34/4/34_466/_article Abstract]
* [2] "Tandem Aldol-Tishchenko Reactions of Lithium Enolates: A Highly Stereoselective Method for Diol and Triol Synthesis" Paul M. Bodnar, Jared T. Shaw, and K. A. Woerpel J. Org. Chem.; 1997; 62(17) pp 5674 - 5675 [http://pubs3.acs.org/acs/journals/supporting_information.page?in_coden=joceah&in_volume=62&in_start_page=5674] [http://pubs.acs.org/subscribe/journals/joceah/suppinfo/62/i17/jo971012e/jo5674.pdf Support information]
Wikimedia Foundation.
2010.
Look at other dictionaries:
Tishchenko reaction — The Tishchenko reaction is a chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide.Ref|1 The reaction product is an ester. Catalysts are aluminium alkoxides… … Wikipedia
Aldol reaction — The aldol reaction is a powerful means of forming carbon–carbon bonds in organic chemistry.[1][2][3] Discovered independently by … Wikipedia
Reacción aldólica de Tishchenko — Saltar a navegación, búsqueda La reacción aldólica de Tishchenko es una reacción de cascada que tiene como participantes a una reacción aldólica y a una reacción de Tishchenko. En síntesis orgánica es un metodo para convertir aldehídos y cetonas… … Wikipedia Español
Cascade reaction — A cascade reaction or tandem reaction or domino reaction is a consecutive series of intramolecular organic reactions which often proceed via highly reactive intermediates. It allows the organic synthesis of complex multinuclear molecules from a… … Wikipedia
Cannizzaro reaction — The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position. [cite journal author = Cannizzaro, S … Wikipedia
Guerbet reaction — The Guerbet reaction, named after Marcel Guerbet (1861 1938), is an organic reaction converting a primary aliphatic alcohol into its β alkylated dimer alcohol with loss of one equivalent of water. [ cite journal title = Condensation de l alcool… … Wikipedia
List of organic reactions — Well known reactions and reagents in organic chemistry include Contents: A B C D E F G H I J K L M N O P Q R S T U V W X Y Z See also Ext … Wikipedia
Carbonyl — In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal… … Wikipedia
Meerwein–Ponndorf–Verley reduction — The Meerwein Ponndorf Verley (MPV) Reduction in organic chemistry is the reduction of ketones and aldehydes to their corresponding alcohols utilizing aluminumalkoxide catalysis in the presence of a sacrificial alcohol[1]. The beauty in the MPV… … Wikipedia
Ethyl acetate — Chembox new Name = Ethyl acetate ImageFile = Ethyl acetate 2D skeletal.png ImageName = Ethyl acetate ImageFile1 = Ethyl acetate 3D balls.png ImageName1 = Ethyl acetate IUPACName = Ethyl ethanoate OtherNames = ethyl ester, acetic ester, ester of… … Wikipedia
