Synfacts 2019; 15(12): 1379
DOI: 10.1055/s-0039-1691107
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Enantioselective Hydroamination of Branched 1,3-Dienes

Mark Lautens
José F. Rodríguez
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
Further Information

Publication History

Publication Date:
18 November 2019 (online)



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.



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.