Ru(II)-catalyzed enantioselective C−H activation/hydroarylation has been developed for the first time, allowing for highly enantioselective synthesis of indoline derivatives via catalytic C−H activation. Commercially available Ru(II) arene complexes and chiral α-methylamines were employed as highly enantioselective catalysts. Based on a sterically rigidified chiral transient directing group, multisubstituted indolines were produced in up to 92% yield with 96% ee. Further transformation of the resulting 4-formylindoline enables access to an optically active tricyclic compound that is of potential biological and pharmaceutical interest.

The results of the bioassays and QSAR studies indicated that the carbon-containing cyclic moiety was the antiviral pharmacophore, and derivative 19, which showed the best inactivation activity, could emerge as a potential antiviral agent against TMV. In vitro capsid protein (CP) assembly and TMV assembly inhibition determinations indicated that these compounds induced crosslinking in the TMV and prevented its uncoating, which was a putative new mode of action for TMV inactivation. © 2018 Society of Chemical Industry.

Developing tandem multiple C–H substitution reactions of simple alkenes provides rapid access to structurally complex unsaturated building blocks. Amidomethylative reactions that reserve CC double bonds have been composed sequentially for tandem catalytic substitutions around the CC bonds of alkenes. As a proof-of-concept demonstration, tandem catalytic amidomethylative processes, which effectively form multiple C–C bonds, have been developed to directly and selectively transform α-substituted styrenes into unsaturated N-heterocycles. Using Fe­(OTf)3 as the sole catalyst, the operationally simple protocols employ bench-stable bisamidomethane as the sole reagent to produce hexahydropyrimidines and 1,2,3,6-tetrahydropyridine derivatives. Moreover, the practical catalytic processes constituted facile two-step pathways, from simple α-substituted styrenes, to access unsaturated 1,3-diamine and bispidine derivatives.

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Catalysis and catalytic cycles are widely used in both research and industry. The addition of a catalysis experiment into the undergraduate laboratory curriculum is important and necessary training to expand student learning. Here, an experiment demonstrating iron-based tandem catalysis was developed and implemented in an organic chemistry course for second-year and upper-division undergraduate students at Mississippi State University. The experiment uses TLC and 1 H NMR to track the reaction and identify the core pharmaceutical structure produced during the experiment. Reactions contained inside the catalytic cycles include iminium generation, imino-ene condensation, and aza-Prins reaction. The catalytic cycle approach allows for a decrease in time for reaction, chemicals, and waste produced. This experiment was successfully tested over two semesters (110 students) at a major university. Learning objectives were met to support student understanding of catalytic cycles and reaction mechanisms. This laboratory experiment provided hands-on experience using TLC and 1 H NMR to identify a core structure of pharmaceutical compounds produced from petroleum.