Synthesis of 1,2-Diamines
The use of a P-spiro chiral arylaminophosphonium barfate and a transition-metal photosensitizer as catalysts enables a redox neutral, highly enantioselective coupling between N-arylaminomethanes and N-sulfonyl aldimines under visible light irradiation. This mode of synergistic catalysis provides a powerful strategy for controlling the bond-forming processes of reactive radical intermediates.
D. Uraguchi, N. Kinoshita, T. Kizu, T. Ooi, J. Am. Chem. Soc., 2015, 137, 13768-13771.
The selective aldimine cross-coupling represents a simple and flexible method for the synthesis of highly substituted unsymmetrical 1,2-diamines. In addition, either the syn- or anti-configurated vicinal diamine can be obtained, depending on the choice of the workup and reduction conditions.
C. Kison, N. Meyer, T. Opatz, Angew. Chem. Int. Ed., 2005, 44, 5662-5664.
A Lewis acid-catalyzed three-component, mild, highly atom econocial, direct-type Mannich reaction of simple aromatic and enolizable aliphatic aldehydes, secondary amines, and glycine derivatives affords various synthetically important anti-α,β-diamino ester derivatives in high yields with high diastereoselectivities.
M. M. Salter, J. Kobayashi, Y. Shimizu, S. Kobayashi, Org. Lett., 2006, 8, 3533-3536.