Iron-catalyzed asymmetric Csp3–H/Csp3–H coupling: improving the chirality induction by mechanochemical liquid-assisted grinding
Literature Information
Tao Ying, Hong Chen, Keyu Xiang, Weike Su, Haijiao Xie, Jingbo Yu
The iron-catalyzed asymmetric oxidative coupling is a challenging transformation that is typically restricted to naphthol substrates (Csp2–H) with carefully designed chiral ligands. Herein, we established a mechanochemical protocol for iron-catalyzed asymmetric Csp3–H/Csp3–H coupling between glycines and β-ketoesters. By using size-tunable liquid additives via non-covalent bond interactions with simply designed chiral salen ligands and substrates under mechanochemical treatment, it is possible to improve the asymmetric induction and offer a variety of structurally diverse α-amino acid derivatives in high enantiopurity. Mechanistic studies revealed that the iminium ion derived from acid-assisted aerobic oxidation of glycine ester was the key intermediate of the reaction, and the liquid additive t-BuOH acted both as a stabilizer for the iminium ion via N–H⋯O interaction and as an assistant for enantio-control. Moreover, a safer, cleaner, and more energy-conserving route via mechanochemically accelerated aging was first disclosed for this asymmetric Csp3–H/Csp3–H coupling reaction.
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Organic Chemistry Frontiers

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry











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