周其林
(1) 不对称催化合成,包括设计合成新型手性配体和手性催化剂,开发新的不对称催化反应;(2) 生物活性的手性天然和非天然化合物合成;(3) 手性药物合成
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- 姓名:周其林
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学术头衔:
博士生导师
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学科领域:
有机化学
- 研究兴趣:(1) 不对称催化合成,包括设计合成新型手性配体和手性催化剂,开发新的不对称催化反应;(2) 生物活性的手性天然和非天然化合物合成;(3) 手性药物合成
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10
周其林, Wen-Jian Shi, Li-Xin Wang, Yu Fu, Shou-Fei Zhu and Qi-Lin Zhou*
Tetrahedron: Asymmetry 14 (2003) 3867-3872,-0001,():
-1年11月30日
The copper complexes of chiral spiro phosphoramidite and phosphite ligands were found to be effective catalysts in the asymmetric allylic alkylations of cinnamyl halides with dialkylzincs. The allylic alkylation products were obtained in high regioselectivities (SN2/SN2 up to 98:2) and enantiomeric excesses of up to 74% for SN2 products.
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周其林, Ai-Guo Hu, Yu Fu, Jian-Hua Xie, Hai Zhou, Li-Xin Wang, and Qi-Lin Zhou*
,-0001,():
-1年11月30日
Optically active a-arylalkylamines are an important class of compounds that are widely used in organic and pharmaceutical synthesis, and much effort has been made to develop efficient asymmetric synthetic methods for them. [1] Asymmetric catalytic hydrogenation of enamides, initiated by Kagan et al., [2] provides a direct and convenient route to chiral amine derivatives. However, many well-known chiral diphosphane ligands, such as DIOP, BINAP, and CHIRAPHOS, which are extremely successful in the asymmetric hydrogenation of dehydroamino acid derivatives, do not give high enantioselectivity in the hydrogenation of enamides.[3, 4] A breakthrough was achieved by Burk et al. [4a] with the introduction of BPE and DuPHOS ligands, which gave excellent enantioselectivity in the Rh-catalyzed asymmetric hydrogenation of enamides. Lately, some other P ligands were also reported to be efficient in the hydrogenation of enamides. [4b, 5] However, all ligands that gave a high degree of enantiocontrol are bidentate. To our knowledge, no efficient chiral monodentate ligand has been reported for the asymmetric hydrogenation of enamides, although some monodentate P ligands were successfully used in the hydrogenation of dehydroamino acid derivatives. [6] Here we describe highly efficient monodentate chiral ligands 1 containing a 1,1 -spirobiindane backbone for the Rh-catalyzed asymmetric hydrogenation of -arylethenylamine derivatives [Eq. (1)] with excellent enantioselectivities (up to 99.7% ee).
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周其林, Zhi-Peng Li a, Fang-Yi Tang a, Hua-Dong Xu a, Xin-Yan Wu a, Qi-Lin Zhou a, b, *, Albert S.C. Chan c
Journal of Molecular Catalysis A: Chemical 193 (2003) 89-95,-0001,():
-1年11月30日
The chiral ligands containing pyridinyl moieties and oxazolines bridged by disubstituted methylene 2-4 were prepared and they provided ee values 17-68% higher than unsubstituted analogues 1 in the palladium-catalyzed enantioselective allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate.
Chiral ligand, Enantioselectivity, Allylic alkylation
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周其林, Jun-An Ma, Jun-Hua Wan, Yi-Bo Zhou, Li-Xin Wang, Wei Zhang, Qi-Lin Zhou*
Journal of Molecular Catalysis A: Chemical 196 (2003) 109-115,-0001,():
-1年11月30日
The dihydrodinaphthazepinyl-oxazoline ligands 3 have been synthesized and tested in the copper-catalyzed enantioselective cyclopropanation of olefins with diazoacetates. The ligands 3 were efficient in the cyclopropanations of styrene derivatives with up to 90% ee. The match of chiralities of binaphthyl and oxazoline in the ligands 3 is crucial for obtaining high enantioselectivity. The absolute configurations of cyclopropanation products were controlled mainly by the configuration of binaphthyl.
Asymmetric catalysis, Cyclopropanation, Dinitrogen ligand, Oxazoline, Azepine
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【期刊论文】Synthesis of Spiro Diphosphines and Their Application in Asymmetric Hydrogenation of Ketones
周其林, Jian-Hua Xie, Li-Xin Wang, Yu Fu, Shuo-Fei Zhu, Bao-Min Fan, Hai-Feng Duan, and Qi-Lin Zhou*
J. AM. CHEM. SOC. 2003, 125, 4404-4405,-0001,():
-1年11月30日
The design of new chiral ligands is the key in the development of transition metal catalyzed asymmetric synthesis.1 Many chiral diphosphine ligands have been prepared and applied in asymmetric catalytic reactions with excellent enantioselectivities. 1,2 Among the chiral diphosphine ligands that have been reported, the atropisomeric C2-symmetric phosphines with a biaryl scaffold initiated by Noyori and co-workers 3 with BINAP were found to have the widest application in the transition metal catalyzed reactions. 4 Planar chiral diphosphines based on ferrocene or paracyclophane backbones have also been applied to a number of reactions with a remarkable degree of success. 5 However, the spiro diphosphine compounds, another type of axially chiral ligands, have not been synthesized until now. 6 Recently, we designed chiral phosphoramidite ligands (SIPHOS) 7 containing a 1,1'-spirobiindane backbone and demonstrated that these ligands can be highly efficient for the Rh-catalyzed asymmetric hydrogenation of functionalized olefins. Especially, in the case of asymmetric hydrogenation of R-arylethenylamines, the spiro monophosphoramidite ligands provided a significantly higher level of enantiocontrol compared to that of the monophosphoramidite ligands derived from BINOL. 7b We now describe the synthesis of spiro diphosphines 6 (SDP) containing 1,1-spirobiindane as a new chiral scaffold and their application in the ruthenium-catalyzed asymmetric hydrogenation of simple ketones with high activity (S/C up to 100 000) and excellent enantioselectivity (ee up to 99.5%).
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周其林, Hai Zhou, Wen-Hu Wang, Yu Fu, Jian-Hua Xie, Wen-Jian Shi, Li-Xin Wang, and Qi-Lin Zhou*
J. Org. Chem. 2003, 68, 1582-1584,-0001,():
-1年11月30日
Novel monodentate chiral spiro phosphoramidite ligands have been readily synthesized in good yields from enantiomerically pure 1,1'-spirobiindane-7, 7'-diol. The new ligands were highly efficient in the copper-catalyzed conjugate addition of Et-Zn to enones with up to 98% enantiomeric excess.
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【期刊论文】Novel monodentate spiro phosphorus ligands for rhodium-catalyzed hydrogenation reactions
周其林, Yu Fu, Jian-Hua Xie, Ai-Guo Hu, Hai Zhou, Li-Xin Wang and Qi-Lin Zhou*
The Royal Society of Chemistry 2002 COMMUN., 2002, 480-481,-0001,():
-1年11月30日
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【期刊论文】Synthesis of chiral bis (oxazolinyl) bipyridine ligands and related helical metal complexes
周其林, Yi-Zhou Zhu, a Zhi-Peng Li, b Jun-An Ma, a Fang-Yi Tang, b Li Kang, b Qi-Lin Zhoua, * and Albert S. C. Chanc
Tetrahedron: Asymmetry 13(2002)161-165,-0001,():
-1年11月30日
Enantiomerically pure tetradentate bis(oxazolinyl)bipyridine ligands 1 have been synthesized in high yields. X-Ray analysis showed that the copper(I) complexes of ligands 1 had a C2-symmetric helical structure. Ruthenium complexes of ligands 1 prepared in situ were found to be efficient in the asymmetric cyclopropanation of styrene with ethyl diazoacetate.
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周其林, Yi-Bo Zhou, a Fang-Yi Tang, b Hua-Dong Xu, b Xin-Yan Wu, b Jun-An Maa and Qi-Lin Zhoua, *
Tetrahedron: Asymmetry 13(2002)469-473,-0001,():
-1年11月30日
Chiral 1,2,3,4-tetrahydroquinolinyl-oxazoline compounds have been synthesized from 8-quinolinecarboxylic acid and enantiomerically pure amino alcohols using a convenient procedure. Asymmetric transfer hydrogenation of aryl ketones with the catalyst prepared in situ from [Ru(p-cymene)Cl2]2 and ligands 2 in 2-propanol in the presence of KOH, afforded the corresponding secondary alcohols in reasonable yields and up to 83% e.e.
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周其林, Shou-Fei Zhu, Yu Fu, Jian-Hua Xie, Bin Liu, Liang Xing and Qi-Lin Zhou*
Tetrahedron: Asymmetry 14(2003)3219-3224,-0001,():
-1年11月30日
Three chiral 4,4'-substituted 1,1'-spirobiindane-7,7'-diols and related monodentate spiro hosphoramidite ligands have been readily synthesized from enantiomerically pure 1,1-spirobiindane-7,7-diol. Excellent enantioselectivities were obtained with these new ligands in the rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives and enamides. Comparing SIPHOS, ligands 4,4'-dibromo-SIPHOS and 4,4'-diphenyl-SIPHOS gave similarly high enantioselectivities although the rates in hydrogenations of enamides are somewhat slower. Methoxy substituents at the 4,4'-position of ligands slightly reduced enantioselectivities of hydrogenation reactions.
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