The Aldol–Tishchenko reaction is a
tandem reaction involving an
aldol reaction and a
Tishchenko reaction. In
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
it is a method to convert
aldehydes and
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
s 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
In organic chemistry, acetyl is a functional group with the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, acetyl is called ethanoyl, ...
[ and propiophenone][ as reactants, the diol is obtained as a pure diastereoisomer.
]
References
{{DEFAULTSORT:Aldol-Tishchenko reaction
Addition reactions
Name reactions