Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide

Peng Yang; Li Hui Lim; Pratanphorn Chuanprasit; Hajime Hirao; Jianrong(Steve) Zhou

doi:10.1002/anie.201606821

Author(s)

Peng Yang
Li Hui Lim
Pratanphorn Chuanprasit
Hajime Hirao
Jianrong(Steve) Zhou

Detail(s)

Original language	English
Pages (from-to)	12083-12087
Journal / Publication	Angewandte Chemie - International Edition
Volume	55
Issue number	39
Online published	30 Aug 2016
Publication status	Published - 19 Sept 2016
Externally published	Yes

Link(s)

DOI	DOI https://doi.org/10.1002/anie.201606821 Final Published version
	Check@CityULib
Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-84992163252&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(487c55f4-b383-42ce-a539-efb5a7e52f89).html

Abstract

An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one-pot synthesis of tetrahydroquinoxalines was also developed starting directly from α-ketoaldehydes and 1,2-diaminobenzene. Formic acid was used as a safe and economic surrogate for high-pressure hydrogen gas. Strongly σ-donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.

Research Area(s)

chiral alkylamines, nickel, reductive amination, synthetic methods, transfer hydrogenation

Citation Format(s)

[ RIS ] [ BibTeX ]

Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide. / Yang, Peng; Lim, Li Hui; Chuanprasit, Pratanphorn et al.
In: Angewandte Chemie - International Edition, Vol. 55, No. 39, 19.09.2016, p. 12083-12087.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62) › 21_Publication in refereed journal › peer-review

Yang, P, Lim, LH, Chuanprasit, P, Hirao, H & Zhou, JS 2016, 'Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide', Angewandte Chemie - International Edition, vol. 55, no. 39, pp. 12083-12087. https://doi.org/10.1002/anie.201606821

Yang, P., Lim, L. H., Chuanprasit, P., Hirao, H., & Zhou, JS. (2016). Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide. Angewandte Chemie - International Edition, 55(39), 12083-12087. https://doi.org/10.1002/anie.201606821

Yang P, Lim LH, Chuanprasit P, Hirao H, Zhou JS. Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide. Angewandte Chemie - International Edition. 2016 Sept 19;55(39):12083-12087. Epub 2016 Aug 30. doi: 10.1002/anie.201606821

Yang, Peng ; Lim, Li Hui ; Chuanprasit, Pratanphorn et al. / Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 39. pp. 12083-12087.