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). 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.

References

  1. ↑ Mitsunori Honda, Ryota Iwamoto, Yoshie Nogami and 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, and 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
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