Enantioselective Synthesis of 5‑Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis
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Enantioselective Synthesis of 5‑Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

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Enantioselective Synthesis of 5‑Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

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Martínez-Pardo, Pablo; Blay Llinares, Gonzalo Perfil; Vila Descals, Carlos; Sanz Marco, Amparo; Muñoz, M. Carmen; Pedro, José Ramón
This document is a artículoDate2019
The first enantioselective formal [3 + 2] cycloaddition between α-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo- and enantioselectivity.

    Martínez-Pardo, Pablo Blay Llinares, Gonzalo Vila Descals, Carlos Sanz Marco, Amparo Muñoz, M. Carmen Pedro, José Ramón 2019 Enantioselective Synthesis of 5‑Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis Journal of Organic Chemistry 84 314 325
https://doi.org/10.1021/acs.joc.8b02808

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