Conjugate Addition of Nitroalkanes to an Acrylate Equivalent. Stereocontrol at C-α of the Nitro Group through Double Catalytic Activation

An unprecedented highly selective direct conjugate addition of prochiral nitroalkanes (R not equal H) to acrylate equivalents is described. The method employs a unique Lewis acid/Bronsted base/MS ternary catalytic system and affords products with dr up to 97/3. With beta-substituted (R' not equal H) acceptors unprecedented levels of antilsyn selectivity (>= 96/4) are attained. Adducts can be transformed into enantioenriched gamma-amino acids and derivatives, Including aldehydes, ketones, lactams, and peptides, through simple protocols with full recovery of camphor auxiliary, the source of chiral information.