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Synfacts 2018; 14(08): 0821
DOI: 10.1055/s-0037-1610488
DOI: 10.1055/s-0037-1610488
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Asymmetric Nickel-Catalyzed Intramolecular Hydroalkenylation
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
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
Further Information
Publication History
Publication Date:
18 July 2018 (online)
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.
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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.
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