Organocatalytic Synthesis of Functionalized Dihydropyrans from Pyruvates in a One-Pot Reaction (No. 0022)

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Dihydropyrans are an important category of compounds, as the structure is present in a variety of pharmaceutical products, as well as other bioactive molecules. Dihydropyran derivatives are commonly synthesized through the non-catalytic reaction of pyruvates at high temperatures, which makes it difficult to control the dual electrophilic/nucleophilic reactivity of pyruvates. Furthermore, this synthetic approach does not allow further functionalization of the product in one pot. A team of OIST researchers led by Prof. Fujie Tanaka has developed a novel, catalytic synthetic route to produce a wide variety of dihydropyran derivatives in one pot from pyruvates and aldehydes, under mild conditions and with high yields and diastereoselectivity.


Lead Researcher:
Fujie Tanaka

Faculty of Chemistry and Chemical Bioengineering Unit


  • Drug discovery
  • Therapeutic medicine



  • A simple, one-pot process
  • Mild conditions (room temperature
  • High yield and diastereoselectivity
  • Large library of potential compounds

Figure 1. (a) The one-pot reaction of pyruvates and aldehydes to generate dihydropyrane derivatives. (b) Further one-pot dihydropyran functionalization routes.

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The researchers showed that the dual reactivities of pyruvates can be managed by using an appropriate catalyst and tuning the reaction conditions, to generate functionalized dihydropyran derivatives in non-enzymatic reactions. The products can be further modified in a one-pot cascade reaction to generate various functionalized molecules. Among the several organocatalysts tested, pyrrolidine-3-carboxylic acid (β-proline) was found to be the best-performing. The optimized reaction was conducted using ethyl pyruvate, aldehyde, and β-proline in CH3CN at 250 oC. Under these conditions, the dihydropyran product was obtained in 72% yield as a single diastereomer.


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