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

References[edit]

  1. ^ Mitsunori Honda; Ryota Iwamoto; Yoshie Nogami; Masahito Segi (2005). "Stereoselective Tandem Aldol–Tishchenko Reaction with Acylsilanes". Chemistry Letters. 34 (4): 466. 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". J. Org. Chem. 62 (17): 5674–5675. doi:10.1021/jo971012e.  Supporting information