Synthesis and reactivity of unsymmetrical azomethine imines formed using alkene aminocarbonylation.

Wei Gan, Patrick J Moon, Christian Clavette, Nicolas Das Neves, Thomas Markiewicz, Amy B Toderian, André M Beauchemin

Center for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.

Organic letters 2013 Apr 19

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Complex cyclic azomethine imines possessing a β-aminocarbonyl motif can be accessed readily from simple alkenes and hydrazones. This alkene aminocarbonylation approach allows formation of ketone-derived azomethine imines of unprecedented complexity. Since unsymmetrical hydrazones are used, two stereoisomers are formed: the reactivity of chiral derivatives is explored in both intra- and intermolecular systems.

Citation

Wei Gan, Patrick J Moon, Christian Clavette, Nicolas Das Neves, Thomas Markiewicz, Amy B Toderian, André M Beauchemin. Synthesis and reactivity of unsymmetrical azomethine imines formed using alkene aminocarbonylation. Organic letters. 2013 Apr 19;15(8):1890-3