Aldol-Tishchenko reaction

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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.

Aldol-tishchenko reaction starting from acetyl trimethylsilane and acetaldehyde


Aldol-tishchenko reaction starting from propiophenone and acetaldehyde

[edit] 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 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 [1] Support information
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