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Synfacts 2009(2): 0166-0166
DOI: 10.1055/s-0028-1087642
DOI: 10.1055/s-0028-1087642
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Mild Protocol for the Synthesis of syn-1,2-Aminonitriles
J. Aydin, C. S. Conrad, K. J. Szabó*
Stockholm University, Sweden
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Januar 2009 (online)
Significance
The traditional alkylation of imines with benzylnitriles is difficult due to easy epimerization or elimination under basic conditions. The reported protocol uses a Pd(II)-pincer complex that activates the nitriles so that deprotonation can occur under unusually mild conditions for this reaction. Thus, a wide range of sulfonylimines 2 can be alkylated with ortho-substituted benzylic nitriles 1. Importantly, preliminary results show that the catalytic process may be rendered enantioselective though the diastereoselectivity is still modest.