Hernando E, Arrayás RG, * Carretero JC. * Universidad Autonóma de Madrid, Spain
Catalytic Asymmetric Mannich Reaction of Glycine Schiff Bases with α-Amido Sulfones as Precursors of Aliphatic Imines.
Chem. Commun. 2012;
48: 9622-9624
Key words
glycine imines - Mannich reaction - copper - Schiff bases
Significance
α,β-Diamino acids are valuable due to their presence in peptide-based drugs and other bioactive compounds. In this report, the authors have extended their copper-catalyzed Mannich reaction of glycine Schiff bases to imines derived from aliphatic aldehydes, which previously performed poorly.
Comment
α-Amido sulfones are employed as imine precursors, due to the instability of imines derived from aliphatic aldehydes. Excellent enantioselectivity and syn-selectivity is obtained for a variety of imines. The products have high synthetic applicability due to the orthogonal protection of the amines.
