The purpose of this research was to synthesize a novel N-heterocyclic carbene (NHC) ligand that can be used in enantioselective catalysis. This NHC ligand will add a second nitrogen, allowing coordination to a metal center in contrast to most NHCs which contain chirality within the ring containing the carbene. Therefore, there will be peripheral chiral centers on the side arm creating improved transfer of stereochemistry due to residing closer to the carbene. Using both the racemic and enantiopure trans-diaminocyclohexane starting material, the novel NHC ligandwas successfully produced through reductive amination and cyclization of an aldehyde and diamine and characterized by 1H-NMR. However, the novel ligand is known to be a grey-brown solid, but it was produced as a dark brown oil. Several methods were attempted to recrystallize the compound, including using acetonitrile, ethyl acetate, and ethanol, but the optimal procedure has not yet been concluded.

Synthesis of a novel N-heterocyclic carbene ligand used for enantioselective catalysis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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