Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope

doi:10.1016/j.tet.2012.03.019

CORC > 化学研究所 > 中国科学院化学研究所

	Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope
	Chen, Fei; Ding, Ziyuan; He, Yanmei; Qin, Jie; Wang, Tianli; Fan, Qing-Hua
刊名	TETRAHEDRON
	2012-07-01
卷号	68 期号:26 页码:5248-5257
关键词	Asymmetric Catalysis Hydrogenation Ruthenium Ketimines Diamine Ligand
ISSN号	0040-4020
DOI	10.1016/j.tet.2012.03.019
英文摘要	Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic eta(6)-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF- anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines in the presence of (Boc)(2)O in dichloromethane or even under solvent-free conditions, providing chiral amines with up to >99% ee and full conversions. Alternatively, the ruthenium catalyst bearing achiral phosphate anion together with corresponding phosphoric acid as the additive was also efficient for the hydrogenation of N-alkyl ketimines in the absence of (Boc)(2)O with excellent enantioselectivities and full conversions. For N-aryl ketimines lower enantiomeric excesses were observed by using the ruthenium catalyst bearing BArF- anion. This catalytic protocol thus provides a facile and practical access to optically active amines and has been successfully employed in the gram-scale synthesis of enantiomerically pure (+)-sertraline. (C) 2012 Elsevier Ltd. All rights reserved.
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000305381700021
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/48291]
专题	中国科学院化学研究所
通讯作者	Fan, Qing-Hua
作者单位	Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Chen, Fei,Ding, Ziyuan,He, Yanmei,et al. Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope[J]. TETRAHEDRON,2012,68(26):5248-5257.
APA	Chen, Fei,Ding, Ziyuan,He, Yanmei,Qin, Jie,Wang, Tianli,&Fan, Qing-Hua.(2012).Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope.TETRAHEDRON,68(26),5248-5257.
MLA	Chen, Fei,et al."Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope".TETRAHEDRON 68.26(2012):5248-5257.