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高景星, Jing-xing Gao a, ), Pian-pian Xu a, Xiao-dong Yi a, Chuan-bo Yang a, Hui Zhang a, Shou-heng Cheng a, Hui-lin Wan a, Khi-rui Tsai a, Takao Ikariya b
Journal of Molecular Catalysis A: Chemical 147, 1999. 105-111,-0001,():
-1年11月30日
The condensation of (S)-propane-1, 2-diamine with two equivalents of o- (diphenylphosphino) benzaldehyde gives (S)-N, N'-bis[o-(diphenylphosphino) benzylidenexpropane-1, 2-diaminew [(S)-1] ligand. The reduction of (S)-1 with excess NaBH4 is carried out in refluxing ethanol to afford corresponding (S)-N, N'-bis [o-(diphenylphosphino) benzylxpropane-1, 2-diamine [(S)-2]. The interaction of trans-RuCl2(DMSO)4 with one equivalent of (S)-1 or (S)-2 in refluxing toluene gives (S)-3 or (S)-4 in good yield, respectively. (S)-1, (S)-2, (S)-3 and (S)-4 have been fully characterized by analytical and spectroscopic methods. The structure of (R)-3 has been also established by an X-ray diffraction study. Catalytic studies showed that (S)-4 as an excellent catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with 90% yield and up to 91% enantiomeric excess.
Chiral ligand, Ruthenium complex, Asymmetric transfer hydrogenation, Ketones
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高景星, Jing-Xing Gao a, ), Xiao-Dong Yi a, Pian-Pian Xu a, Chun-Liang Tang a, Hui Zhang a, Hui-Lin Wan a, Takao Ikariya b
Journal of Molecular Catalysis A: Chemical 159, 2000. 3-9,-0001,():
-1年11月30日
The interaction of [Rh(COD)Cl]2 with two equivalents of (S)-N,NX-biswo-( diphenylphosphino) benzylidenexpropane-1, 2-diamine [(S)-1] or (S)-N, N'-bis [o-(diphenylphosphino) benzylxpropane-1, 2-diamine [(S)-2] in benzene/methanol mixture and then precipitation by the addition of a solution of NH4PF6 in water afforded cationic rhodium (I) complexes [Rh(S)-MeP2N2] [PF6] and [Rh(S)-MeP2 (NH)2] [PF6] in good yield, respectively. Complexes [Rh(R,R)-C6P2N2] [PF6] and [Rh(R,R)-C6P2(NH)2] [PF6] were also prepared by an analogous manner. All these rhodium complexes have been characterized by analytical and spectroscopic methods and their asymmetric catalytic properties for enantioselective transfer hydrogenation of acetophenone have been tested. [Rh(R,R)-C6P2(NH)2] [PF6] was used as an excellent catalyst precursor for enantioselective transfer reduction of acetophenone in 2-propanol, leading to 2-phenylathanol in 97% yield and in 91% ee after 7 h at 83℃.
Cationic rhodium complexes, Enantioselective reduction, Simple ketones
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高景星, Hui Zhang, a Chuan-Bo Yang, a Yan-Yun Li, a Zhen-Rong Dong a, a Jing-Xing Gao, *a Hideaki Nakamura, b Kunihiko Murata b and Takao Ikariya*b
CHEM. COMMUN., 2003, 142-143,-0001,():
-1年11月30日
The chiral Ru cluster-based catalyst systems generated in situ from Ru3(CO)12 and chiral iiminodiphosphine tetradentate ligands effected asymmetric transfer hydrogenation of propiophenone in 2-propanol, leading to 1-phenyl-1-propanol in 94% yield and with 96% ee.
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高景星, Jing-Xing Gao, ‡ Takao Ikariya, § and Ryoji Noyori*, §, |
Organometallics 1996, 15, 1087-1089,-0001,():
-1年11月30日
Summary: The trans-RuIICl2 complexes with structurally similar N,N¢-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine and N,N¢-bis[o-(diphenylphosphino)-benzyl]cyclohexane-1,2-diamine ligands have been synthesized, and their molecular structures have been determined. The C2-symmetric diphosphine/diaminebased Ru complex acts as an excellent catalyst precursor in asymmetric transfer hydrogenation of acetophenone in a 0.1 M 2-propanol solution, leading to 2-phenylethanol in 97% ee and in 93% yield after 7h at 45℃. This transfer hydrogenation is characterized by low reversibility under these conditions.
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【期刊论文】New Chiral Catalysts for Reduction of Ketones
高景星, JING-XING GAO, * HUI ZHANG, XIAO-DONG YI, PIAN-PIAN XU, CHUN-LIANG TANG, HUI-LIN WAN, KHI-RUI TSAI, AND TAKAO IKARIYA
CHIRALITY 12: 383-388 (2000),-0001,():
-1年11月30日
The condensation of o-(diphenylphosphino)benzaldehyde and various chiral diamine gives a series of diimino-diphosphine tetradentate ligands, which are reduced with excess NaBH4 in refluxing ethanol to afford the corresponding diaminodiphosphine ligands in good yield. The reactivity of these ligands toward trans-RuCl2(DMSO)4 and [Rh(COD)Cl]2 had been investigated and a number of chiral Ru(II) and Rh(I) complexes with the PNNP-type ligands were synthesized and characterized by microanalysis and IR, NMR spectroscopic methods. The chiral Ru(II) and Rh(I) complexes have proved to be excellent catalyst precursors for the asymmetric transfer hydrogenation of aromatic ketones, leading to optically active alcohols in up to 97% ee. Chirality 12: 383-388, 2000.
ruthenium, rhodium, chiral amino/, phosphine ligands, asymmetric catalysis, ketones, alcohols, enantioselective hydrogenations
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