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

Summary

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.

Applications

• Drug discovery
• Therapeutic medicine

Advantages

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