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Issue 10, 2013
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First diastereoselective [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides

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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 4. The diastereoselectivity of the cycloaddition reaction was rationalised by theoretical studies.

Graphical abstract: First diastereoselective [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides

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Publication details

The article was received on 07 Sep 2012, accepted on 14 Jan 2013 and first published on 14 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB26766K
Org. Biomol. Chem., 2013,11, 1640-1649

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    First diastereoselective [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides

    C. Arróniz, J. Molina, S. Abás, E. Molins, J. M. Campanera, F. J. Luque and C. Escolano, Org. Biomol. Chem., 2013, 11, 1640
    DOI: 10.1039/C3OB26766K

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