Fig. 2: Development of effective non-covalent π interactions between the catalyst and the alkene substrate for AD-based kinetic resolution. | Nature Communications

Fig. 2: Development of effective non-covalent π interactions between the catalyst and the alkene substrate for AD-based kinetic resolution.

From: Engineered non-covalent π interactions as key elements for chiral recognition

Fig. 2

a Using cinchona alkaloid ligand A with the piperonylate moiety as a large, delocalized π system in AD-based kinetic resolution. b Proposed possible π–π interactions in the racemic alkene substrates/Ligand A-OsO4 complexes. c Screening an appropriate π moiety in the alkene substrate that could establish desired π–π interactions with the piperonylate moiety in ligand A. General condition: K2OsO2(OH)4 (0.4 mol%), K3Fe(CN)6 (3.0 equiv), K2CO3 (3.0 equiv), ligand A (1.0 mol%) and alkene (0.1 mmol) in 1.0 mL tBuOH-H2O (v/v = 1:1), 0 °C. s: selectivity factor; s = In[(1 − c)(1 − ee)]/In[(1 − c)(1+ee)]. Conversion (conv) was determined by 1H NMR analysis of the crude mixture.

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