Organocatalytic Asymmetric Aldol Reaction of Arylglyoxals and Hydroxyacetone: Enantioselective Synthesis of 2,3-Dihydroxy-1,4-diones

Abstract

A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.

Recyclable Organocatalysts in Asymmetric Synthesis

“…A great interest has been arised to enhance these precious chiral structures to achieve remarkable results in asymmetric synthesis [1–5] . Countless studies have been done in many different types of reactions such as Michael, [5–9] aldol, [10–16] Diels‐Alder, [17–21] Henry, [22–27] aza‐Henry, [28–33] Friedel‐Crafts, [34–38] Povarov, [39–42] decarboxylative Doebner‐Knoevenagel [43,44] reactions and many others. Although asymmetric organocatalysis can be considered as the most successful and easy way to synthesize enantioenriched compounds, [45] one of the most debated drawbacks is the possibility of agglomeration and aggregation due to high catalyst loading in the reactions.…”