NAGIOS: RODERIC FUNCIONANDO
Catalytic Diastereo- and Enantioselective Synthesis of 2‑Imidazolinones
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Catalytic Diastereo- and Enantioselective Synthesis of 2‑Imidazolinones
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| Martínez-Pardo, Pablo; Blay Llinares, Gonzalo Perfil; Escrivá-Palomo, Alba; Sanz Marco, Amparo; Vila Descals, Carlos; Pedro, José Ramón | |
| This document is a artículoDate2019 | |
| 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, Pablo Blay Llinares, Gonzalo Escrivá-Palomo, Alba Sanz Marco, Amparo Vila Descals, Carlos Pedro, José Ramón 2019 Catalytic Diastereo- and Enantioselective Synthesis of 2‑Imidazolinones Organic Letters 21 4063 4066 |
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| https://doi.org/10.1021/acs.orglett.9b01244 |
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