Litcius/Paper detail

Direct Asymmetric Three-Component Mannich Reaction Catalyzed by Chiral Counteranion-Assisted Silver

Zhongyou Yin, Zhixiong Guo, Rui Zhang, Xiaoyun Hu, Victor Borovkov

2020The Journal of Organic Chemistry22 citationsDOI

Abstract

Direct asymmetric three-component Mannich reaction involving simple ketones (such as cyclohexanone, acetone, and acetophenone) as donors and catalyzing by silver tartaric acid-derived phosphate was realized to afford a series of optically active β-amino-ketone derivatives in high yields (up to 96%) and good-to-high enantioselectivities (up to 97%) with moderate-to-good diastereoselectivities. This is the first example of direct catalytic asymmetric three-component Mannich reaction via a chiral counteranion-directed strategy.

Topics & Concepts

ChemistryCyclohexanoneAcetophenoneMannich reactionKetoneCatalysisAcetoneTartaric acidComponent (thermodynamics)Organic chemistryCombinatorial chemistryDiastereomerAldol reactionCitric acidPhysicsThermodynamicsAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisAsymmetric Hydrogenation and Catalysis