Carbon-hydrogen bond functionalization reactions are useful in building molecular complexity while maintaining efficient step and atom economies. We recently reported that oxoammonium-based hydride abstracting agents, such as Bobbitt’s Salt, can efficiently oxidize allyl carbamate substrates to access the valuable acyl iminium ion intermediate. This process can yield nitrogen-containing heterocycles when the oxidation is coupled with a carbon-carbon bond forming step, which are attractive targets in natural product synthesis. Accessing acyl iminium ions through oxidation of an allyl amide or carbamate greatly increases functional group compatibility and ease of synthesis compared to previously reported methods. Described in this poster is the transition metal-free oxidative C-H bond functionalization of allyl carbamates, amides, and sulfonamides via hydride abstraction by oxoammonium salts to access piperidine-type heterocycles in a diastereoselective manner. The scope and utility of this method were explored, as well as the unique structures of the cyclized products.

Stereoselective piperidine synthesis via oxidative carbon-hydrogen bond functionalization of allyl carbamates, amides, and sulfonamides by Bobbitt's salt

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