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An approach towards (+)-allokainic acid via diphenylprolinol-catalyzed direct cross-aldol reaction

Shashank N Mhaldar1,2, Santosh G Tilve1

  • 1School of Chemical Sciences, Goa University, Taleigao Plateau, Goa, 403206, India. stilve@unigoa.ac.in.

Organic & Biomolecular Chemistry
|June 20, 2023
PubMed

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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
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