Tran G,
Shao W,
Mazet C.
* University of Geneva, Switzerland
Ni-Catalyzed Enantioselective Intermolecular Hydroamination of Branched 1,3-Dienes
Using Primary Aliphatic Amines.
J. Am. Chem. Soc. 2019;
141: 14814-14822
Key words
nickel catalysis - hydroamination - 1,3-dienes
Significance
The authors report an enantioselective hydroamination of 1,3-dienes by using nickel
catalysis. The products were obtained in moderate to good yields and with high enantioselectivities.
Reaction monitoring, deuterium labelling, and kinetic studies were performed to elucidate
the reaction mechanism.
Comment
Mechanistic experiments reveal the irreversibility of this reaction. Deuterium incorporation
was observed in the hydroaminated product when d
2-benzylamine and d
1-TFE were employed. Kinetic studies suggest that a Ni–π-allyl species arising from
hydronickelation is the catalyst resting state.
