Highly diastereoselective nitroaldol reactions with chiral derivatives of glyoxylic acid

N-Glyoxyloyl-(2R)-bornane-10,2-sultam (1a) and (1R)-8-phenylmenthyl glyoxylate (1b) react stereoselectively with simple nitroalkanes giving diastereomeric nitroalcohols with high asymmetric induction. The glyoximide 1a is proved to be a highly efficient chiral inducer, superior to glyoxylate 1b. In all cases, the absolute configuration (2S) and relative configuration, syn for the major diastereoisomers, were confirmed.