Synthesis of New Chiral Hydrogenated Quinolinyl-Oxazoline Ligands

Chem. J. Chinese Universities ›› 2001, Vol. 22 ›› Issue (S1): 130.

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Synthesis of New Chiral Hydrogenated Quinolinyl-Oxazoline Ligands

ZHOU Yi-Bo, DUAN Xue-Xin, ZHOU Qi-Lin

Stale Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

Received:2001-08-01 Online:2001-12-31 Published:2001-12-31
Contact: qlzhou@public.tp.tj.cn E-mail:qlzhou@public.tp.tj.cn

Abstract

Abstract:

Chiral hydrogenated quinolinyl-oxazoline ligands 2a-c were synthesized from 8-quinolinyl carboxylic acid and chiral amino alcohols. The complex formed from [RuCl₂(cymene)] and of 2c acts as an catalyst in asymmetric hydrogenation of acetophenone in #em/em#-PrOH, leading to 2-phenylethanol in 44%ee and 71% isolated yield. The optimizations of the reaction are ongoing in our laboratory.

Key words: Chiral ligand, Hydrogenated quinolinyl-oxazoline, Asymmetric transfer hydrogenation

CLC Number:

O625

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ZHOU Yi-Bo, DUAN Xue-Xin, ZHOU Qi-Lin. Synthesis of New Chiral Hydrogenated Quinolinyl-Oxazoline Ligands[J]. Chem. J. Chinese Universities, 2001, 22(S1): 130.

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[1]	CHEN Danyi, ZHANG Fumei, HE Dan, ZHANG Zimei, ZHONG Fen, WEN Simiaomiao, LIU Qixing, ZHOU Haifeng. Synthesis of Chiral Phenylbenzothiazole Methanol via Transfer Hydrogenation Catalyzed by Ruthenium Complexes^† [J]. Chem. J. Chinese Universities, 2020, 41(10): 2264.
[2]	XU Cong, HU Wenhao. Recent Advances of ChiraI Spiro Ligands and Their Catalysts in Asymmetric Catalysis^† [J]. Chem. J. Chinese Universities, 2020, 41(10): 2153.
[3]	SUN Yang, ZHANG Lei, XU Fei, GONG Bo-Lin. Preparation of Chiral Ligand Exchange Chromatographic Stationary Phase by Atom Transfer Radical Polymerization for Separation of Racemates [J]. Chem. J. Chinese Universities, 2012, 33(12): 2644.
[4]	ZHAO Jin-Feng, DOU Hai-Jian, ZHOU Yu-Han, QU Jing-Ping*. Asymmetric Transfer Hydrogenation of β-Amino Ketone Catalyzed by (S,S)-TsDPEN-Ru Complex and Its Application in the Synthesis of Duloxetine [J]. Chem. J. Chinese Universities, 2011, 32(10): 2331.
[5]	MING Yan-Hua, FAN Ai-Li, JIN Zi-Lin, JIANG Jing-Yang*. Synthesis of Thermoregulated Noyori Ligand and Its Application in Asymmetric Transfer Hydrogenation of Acetophenone [J]. Chem. J. Chinese Universities, 2010, 31(8): 1548.
[6]	YUAN Jian-Chao, ZHANG Yu-Hua, CHEN Min-Dong, LÜ Shi-Jie, Wang-Dong-Mei . Synthesis and Characterization of Main Chain Optically Active Copolymer of ω-Undecylenic Acid with Carbon Monooxide [J]. Chem. J. Chinese Universities, 2001, 22(7): 1152.
[7]	LONG Yuan-De, WANG Qun-Biao, HUANG Tian-Bao . A Novel Bonded Stationary Phase for Chiral Ligand Exchange-Chromatography [J]. Chem. J. Chinese Universities, 2001, 22(4): 566.
[8]	PENG Yun-Gui, FENG Xiao-Ming, WANG Bin, LI Zhi, YANG Gui-Shu, JIANG Yao-Zhong. A Study of Asymmetric Baeyer-Villiger Reaction of 2-Phenylcyclohexanone Catalyzed by Chiral Salen-Cu(Ⅱ) and Oxazoline-Cu(Ⅱ) Complexes [J]. Chem. J. Chinese Universities, 2001, 22(2): 223.
[9]	YAO Jin-Shui, XU Gui-Yun, Li Hong, He Bing-Lin. Studies on the Chiral Structure of Thiazolidine Ligands and Their Application to Asymmetric Hydrosllylation Of Acetophenone [J]. Chem. J. Chinese Universities, 1998, 19(11): 1763.