Hydroamination is the atom economical addition of a N-H bond across an unsaturated C-C bond. When the substrate is an aminoallene, the product of the reaction contains a stereogenic center. Early metal complexes with chiral bidentate amide-alkoxide ligands have been used to catalyze the asymmetric hydroamination of aminoallenes with high enantioselectivity. The catalytic reaction is thought to proceed through a [2+2] cycloaddition and DFT calculations have been performed to examine ground and transition state energies. The impact of temperature and metal-to-ligand ratio on the enatioselectivity of this reaction will be discussed, as well as future synthetic directions suggested by theory.

Asymmetric hydroamination with titanium and tantalum: experiment and theory

249th National Meeting (2015)

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