Catalytic Diastereo- and enantioselective vinylogous Mannich reaction of alkylidenepyrazolones to isatin-derived ketimines
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Catalytic Diastereo- and enantioselective vinylogous Mannich reaction of alkylidenepyrazolones to isatin-derived ketimines

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Catalytic Diastereo- and enantioselective vinylogous Mannich reaction of alkylidenepyrazolones to isatin-derived ketimines

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Carceller-Ferrer, Laura; Vila Descals, Carlos; Blay Llinares, Gonzalo Perfil; Muñoz, M. Carmen; Pedro, José Ramón
This document is a artículoDate2021
A valuable organocatalytic vinylogous Mannich reaction between alkylidenepyrazolones and isatin-derived ketimines has been successfully established. Squaramide organocatalyst, prepared from quinine, catalyzed the diastereo- and enantioselective vinylogous Mannich addition, affording a range of aminooxindole-pyrazolone adducts (24 examples) with excellent outcomes: up to 98% yield with complete diastereoselectivity and excellent enantioselectivity (up to 99% ee). Additionally, different synthetic transformations were performed with the chiral pyrazolone-oxindole adducts.

    Carceller-Ferrer, Laura Vila Descals, Carlos Blay Llinares, Gonzalo Muñoz, M. Carmen Pedro, José Ramón 2021 Catalytic Diastereo- and enantioselective vinylogous Mannich reaction of alkylidenepyrazolones to isatin-derived ketimines Organic Letters 23 19 7391 7395
https://doi.org/10.1021/acs.orglett.1c02571

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