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.
References
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{{cite journal |title=Stereoselective Tandem Aldol–Tishchenko Reaction with Acylsilanes |author1=Mitsunori Honda |author2=Ryota Iwamoto |author3=Yoshie Nogami |author4=Masahito Segi |journal=Chemistry Letters |volume=34 |year=2005 |issue=4 |pages=466–467 |doi=10.1246/cl.2005.466}}
{{cite journal|title=Tandem Aldol–Tishchenko Reactions of Lithium Enolates: A Highly Stereoselective Method for Diol and Triol Synthesis|author1=Paul M. Bodnar |author2=Jared T. Shaw |author3=K. A. Woerpel |journal=Journal of Organic Chemistry|year=1997|volume= 62|issue=17|pages= 5674–5675|doi=10.1021/jo971012e}} [http://pubs.acs.org/subscribe/journals/joceah/suppinfo/62/i17/jo971012e/jo5674.pdf Supporting information]
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