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

Asymmetric nitroaldol reaction of alpha-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 alpha-ketoesters to construct the adjacent stereocenters of the chiral tertiary alcohol product with high diastereo- and enantio selectivity. (c) 2008 Elsevier Ltd. All rights reserved.