Organocatalytic asymmetric Michael addition of pyrazoleamides to beta-phthalimidonitroethene

A highly organocatalyzed asymmetric Michael addition reaction of pyrazoleamides to beta-phthalimidonitroethene has been developed with a chiral bifunctional thiourea-tertiary amine as the catalyst. A wide range of gamma-nitro beta-amino amides were readily obtained in good to excellent yields with high diastereo-and enantioselectivities (up to 99% yield, 99% ee and >20:1 dr). The large scale experiment and transformation of the product have also been demonstrated. (C) 2017 Elsevier Ltd. All rights reserved