Aldol–Tishchenko reaction
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(Redirected from Tishchenko–Claisen 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), to which a suitable aldehyde is added. The resulting 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.
![Aldol–Tishchenko reaction starting from acetyl trimethylsilane and acetaldehyde](http://up.wiki.x.io/wikipedia/commons/thumb/f/f0/Aldol%E2%80%93Tishchenko-scheme1.png/600px-Aldol%E2%80%93Tishchenko-scheme1.png)
![Aldol–Tishchenko reaction starting from propiophenone and acetaldehyde](http://up.wiki.x.io/wikipedia/commons/thumb/1/14/Aldol%E2%80%93Tishchenko-scheme2.png/600px-Aldol%E2%80%93Tishchenko-scheme2.png)
References
[edit]- ^ Mitsunori Honda; Ryota Iwamoto; Yoshie Nogami; Masahito Segi (2005). "Stereoselective Tandem Aldol–Tishchenko Reaction with Acylsilanes". Chemistry Letters. 34 (4): 466–467. doi:10.1246/cl.2005.466.
- ^ Paul M. Bodnar; Jared T. Shaw; K. A. Woerpel (1997). "Tandem Aldol–Tishchenko Reactions of Lithium Enolates: A Highly Stereoselective Method for Diol and Triol Synthesis". Journal of Organic Chemistry. 62 (17): 5674–5675. doi:10.1021/jo971012e. Supporting information