A one-pot regioselective two C-C bonds forming dearomatization of pyridines and quinolines is disclosed. Two 3,4betaines are identified for the first time as very useful organic synthons in heterocyclic chemistry. Furthermore, the chemical reactivity of the prepared trifluoromethyl ketones, a new type of push-pull enones, has been explored to develop straightforward methods for their functionalization. This protocol represents a breakthrough in the dearomatization of heteroaromatics as both the selective saturation and functionalization of heteroaromatics are achieved in high efficiency by the attachment of two substituents, including the valuable trifluoromethyl ketone group.

A regioselective one-pot approach to the synthesis of C4-alkylated tetrahydropyridines (THPs) and tetrahydroquinolines (THQs) by dearomatization of pyridines and quinolines has been developed. The transformation is achieved by the BF 3 • OEt 2-mediated, C4-selective addition of Grignard reagents, followed by a cascade of enamine protonation and the subsequent Et 3 SiH reduction of the resulting iminium ions. This protocol not only provides a facile synthetic approach to C4-substituted THPs and THQs, but also offers a new strategy for the dearomatization of heteroaromatics.

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Nine complex diterpenes were synthesized using a hybrid oxidative approach that combines chemical and enzymatic C–H oxidation methods.

We report a metal-free and stereoselective four-component reaction between α-ketoamides, amines, aromatic aldehydes and β-nitroalkenes or β-pivaloxy-nitroalkanes to obtain 2,3-dihydro-4-nitropyrroles functionalized in every position. The heterocycles accessible using this reaction may have utility in the synthesis of pharmacologically active compounds.