title: Conjugate addition of nitroalkanes to an acrylate equivalent. Stereocontrol at C-alpha of the nitro group through double catalytic activation.
abstract: 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/Brønsted 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 anti/syn selectivity (>or=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.
authors: Departamento de Química Aplicada, Universidad Pública de Navarra, Pamplona, Spain.
authors: Jesús M
authors: JM
authors: García
authors: Miguel A
authors: MA
authors: Maestro
authors: Mikel
authors: M
authors: Oiarbide
authors: José M
authors: JM
authors: Odriozola
authors: Jesús
authors: J
authors: Razkin
authors: Claudio
authors: C
authors: Palomo