Asymmetric organocatalytic nitroaldol reaction of α-ketoesters: stereoselective construction of chiral tertiary alcohols at subzero temperature

Abstract Asymmetric nitroaldol reaction of α-ketoesters was explored using a guanidine–thiourea bifunctional organocatalyst at temperatures below the freezing point of water. The new reaction protocol can be applied to the nitroaldol reaction of nitroalkanes and α-ketoesters to construct the adjacent stereocenters of the chiral tertiary alcohol product with high diastereo- and enantioselectivity.