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Synfacts 2008(1): 0050-0050
DOI: 10.1055/s-2007-991480
DOI: 10.1055/s-2007-991480
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Activation of tropos Ligands in the Strecker Reaction
J. Wang, X. Hu, J. Jiang, S. Gou, X. Huang, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)
Significance
The catalytic asymmetric Strecker reaction is an important reaction in the synthesis of chiral amino acids. The authors report on a highly selective catalytic method for the cyanation of N-tosyl-protected aldimines and ketimines which yield tertiary or quaternary α-amino nitriles in high yields and ee. The key is the use of a flexible biphenol ligand in combination with a readily available chiral modifier. The atropos ligand is influenced by the chiral modifier and directs the ligand to the most stable conformation, which then defines the enantiodiscrimination of the catalytic center.