The molybdenum complex {TpMo(NO)(DMAP)} (where Tp = hydridotris(pyrazolyl)borate and DMAP = 4-(dimethylamino)pyridine) is able to bind aromatic molecules and promote reactions on the bound ring system.<sup>1,2</sup> This bulky, electron-rich metal complex allows for additions with high regio- and stereoselectivity. Despite the high selectivity imbued by the bulky metal center, the racemic nature of the metal complex ensures racemic organic products. Current research efforts are focused on resolving one enantiomer of the metal complex to allow for synthesis of enantiopure organic products. Coordination of the chiral terpene α-pinene to the metal scaffold produces a single diastereomer, and consequently, a single enantiomer of the metal center. Unfortunately, exchanging the pinene ligand for a more synthetically interesting aromatic ring, the metal center racemizes. It was found that addition of a noncoordinating, single electron oxidant was able to catalyze the exchange reaction with complete retention of the metal center. Current methodology allows for catalytic reactions to bind aldehydes and ketones. The application of this technique to synthesize enantiopure arene systems is currently under investigation

Enantioenrichment of a molybdenum dearomatization agent by redox catalysis

255th National Meeting (2018)

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