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Synfacts 2007(7): 0715-0715
DOI: 10.1055/s-2007-968613
DOI: 10.1055/s-2007-968613
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Zinc-Catalyzed Asymmetric Synthesis of anti-1,2-Nitroamines
B. M. Trost*, D. W. Lupton
Stanford University, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Juni 2007 (online)
Significance
The asymmetric aza-Henry reaction is a new application of the dinuclear metal catalyst 3 developed by the Trost group. Although Shibasaki has carried out seminal studies on the addition of nitroenolates to C=N groups, the method expands the scope of the imine reacting partner to encompass a range of α-substituents to the imine, as well as the nature of the nitrogen protecting group. Of particular synthetic interest are α,β-unsaturated adducts like 9 and 10. The α-nitroamines 4-10 obtained are useful precursors to chiral 1,2-diamines by reduction, or to α-amino acids by oxidative cleavage.