Li K.
Li M.-L.
Zhang Q.
Zhu S.-F.
*
Zhou Q.-L.
* Nankai University and the Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P. R. of China
Highly Enantioselective Nickel-Catalyzed Intramolecular Hydroalkenylation of N- and O‑Tethered 1,6-Dienes to Form Six-Membered Heterocycles.
J. Am. Chem. Soc. 2018;
140: 7458-7461
Key words
nickel catalysis - hydroalkenylation - piperidines
Significance
Nickel catalysis has been explored in recent years as a cost-effective alternative to palladium. Zhu, Zhou, and co-workers report the enantioselective nickel-catalyzed isomerizations of dienes to yield chiral piperidines or tetrahydropyrans, which are found in a number of natural products and drug structures.
Comment
The reaction was proposed to involve a nickel-hydride intermediate, which was generated through β-hydride elimination of the alkyl nickel species. The approach was successful with a variety of substituents on the olefin, and all the reactions proceeded with high enantioselectivities.
