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), 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
Aldol–Tishchenko reaction starting from acetyl trimethylsilane and acetaldehyde
Aldol–Tishchenko reaction starting from propiophenone and acetaldehyde
Aldol–Tishchenko reaction starting from propiophenone and acetaldehyde

References

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  1. ^ 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.
  2. ^ 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