Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of 1,2-Diamines
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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.
C. Kison, N. Meyer, T. Opatz, Angew. Chem. Int. Ed., 2005,
44, 5662-5664.
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.
