| Popis: |
The imide functionality, as part of chiral and achiral auxiliaries such as oxazolidinones, has played a key role in numerous asymmetric organic reactions. In this chapter, stereoselective conjugate additions of N–N and N–O nucleophiles to α,β-unsaturated imides are reviewed. The reactions of alkylhydrazines, oximes, O-substituted hydroxylamines, and N-substituted hydroxylamines are covered with attention to the chiral components (such as Lewis acid catalyst or imide structure) responsible for stereoinduction and the stereochemical models proposed in the literature for the observed selectivity. Further transformations of the conjugate addition products are briefly discussed in light of their relevance to the synthesis of potentially bioactive structures such as β-amino acids. |
