Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones

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Abstract

Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.

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Martínez-Pardo, P., Blay, G., Escrivá-Palomo, A., Sanz-Marco, A., Vila, C., & Pedro, J. R. (2019). Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones. Organic Letters, 21(11), 4063–4066. https://doi.org/10.1021/acs.orglett.9b01244

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