Highly diastereoselective Henry reaction of nitro compounds with chiral derivatives of glyoxylic acid

Abstract N -Glyoxyloyl-(2 R )-bornane-10,2-sultam and (1 R )-8-phenylmenthyl glyoxylate react stereoselectively with simple nitro compounds giving diastereoisomeric nitroalcohols with high asymmetric induction. N -Glyoxyloyl-(2 R )-bornane-10,2-sultam 1a is shown to be a highly efficient chiral inducer, superior to (1 R )-8-phenylmenthyl glyoxylate 1b . In all cases, the absolute (2 S ) configuration at the center bearing the hydroxy group and the relative syn configuration for the major diastereoisomers were determined.