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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), 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 and propiophenone as reactants, the diol is obtained as a pure diastereoisomer.

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

References

References

  1. (2005). "Stereoselective Tandem Aldol–Tishchenko Reaction with Acylsilanes". [[Chemistry Letters]].
  2. (1997). "Tandem Aldol–Tishchenko Reactions of Lithium Enolates: A Highly Stereoselective Method for Diol and Triol Synthesis". [[Journal of Organic Chemistry]].
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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