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  • Title: First diastereoselective [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides.
    Author: Arróniz C, Molina J, Abás S, Molins E, Campanera JM, Luque FJ, Escolano C.
    Journal: Org Biomol Chem; 2013 Feb 13; 11(10):1640-9. PubMed ID: 23358611.
    Abstract:
    Bicyclic α-iminophosphonates were prepared via the first diastereoselective silver catalyzed [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and diversely N-substituted maleimides. The reduction of the resulting imine by catalytic hydrogenation led to cyclic α-aminophosphonates, which are α-aminoester surrogates. The relative stereochemistry of the adducts was confirmed by X-ray crystallographic analysis of . The diastereoselectivity of the cycloaddition reaction was rationalised by theoretical studies.
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