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Ferrocene derivative and application thereof

A kind of technology of ferrocene derivative and alkyl group, applied in the field of ferrocene derivative

Inactive Publication Date: 2012-09-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, compared with enzymes, these non-enzyme catalysts have better universality for substrates, but none of them can achieve the effect of enzymes in terms of selectivity.

Method used

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  • Ferrocene derivative and application thereof
  • Ferrocene derivative and application thereof
  • Ferrocene derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Synthesis of 2-chloroazaidenyl-pentaphenylcyclopentadienyl iron racemate (compound shown in formula VIa-1, abbreviated as compound VIa-1, the same below):

[0041]

[0042]

[0043] Under the protection of high-purity nitrogen, butyllithium (3.44mL, 5.5mmol) was slowly added dropwise with a syringe to a solution of pentaphenylcyclopentadiene (2.45g, 5.5mmol) in anhydrous tetrahydrofuran (20mL) cooled in an ice bath (1.6mol / L, the solvent is n-hexane,), and the dropping time is 10 minutes. During the dropwise addition, the solution gradually changed from heterogeneous to homogeneous, and the color turned yellow. After the dropwise addition was completed, the reaction was continued for 2 hours in an ice bath until the solution became completely clear and orange-yellow;

[0044] Under the protection of high-purity nitrogen, anhydrous tetrahydrofuran (10 mL) was added to anhydrous ferrous chloride (693 mg, 5.5 mmol) cooled in an ice bath. Stirring was continued ...

Embodiment 2

[0072] (1) Synthesis of (SSp)-2-((1-phenyl-2-hydroxy)ethylamino)-azaidenyl-pentamethylcyclopentadienyliron (compound VIIIb-2):

[0073]

[0074] Substituting pentamethylcyclopentadiene for pentaphenylcyclopentadiene in step (1) of Example 1, repeating steps (1) to (3) in Example 1 to obtain compound VIIIb-2 with a yield of 93 %.

[0075] 1 H NMR (400MHz, CDCl 3 ): δ7.67(d, J=8.8Hz, 1H), 7.50(d, J=6.8Hz, 2H), 7.37(dd, J=6.8Hz, 2H), 7.31(dd, J=6.8Hz, 1H ), 6.58(d, J=8.8Hz, 1H), 4.54(d, J=9.6Hz, 1H), 4.46(s, 2H), 4.30(dd, J 1 =8.4Hz,J 2 =9.2Hz; 2H), 4.07(s, 1H), 3.73(s, 1H), 1.67(s, 15H).

[0076] (2) (SSp)-2-phenyl-2,3-dihydroimidazole-[1,2-a]-pyridine-[e]-cyclopentenyl-pentamethylcyclopentadienyliron (compound Synthesis of Ib-2):

[0077]

[0078] Substituting Compound VIIIb-2 for Compound VIIIb-1 in Step (4) of Example 1, and repeating Step (4) in Example 1 to obtain Compound Ib-2 with a yield of 92%.

[0079] 1 H NMR (400MHz, CDCl 3 ): δ7.33(d, J=4Hz, 4H), 7.2...

Embodiment 3

[0081] (SSp)-2-isopropyl-2,3-dihydroimidazole-[1,2-a]-pyridine-[e]-cyclopentenyl-pentaphenylcyclopentadienyliron (compound I b -3) synthesis:

[0082]

[0083] Replace (R)-4-phenyl-oxazolin-2-one in the step (2) of embodiment 1 with (R)-4-isopropyl-oxazolin-2-one, repeat embodiment 1 Steps (1)-(4) yielded compound Ib-3 with a yield of 93%.

[0084] 1 H NMR (400MHz, CDCl 3 ): δ7.17-7.13(m, 5H), 7.09-7.05(m, 10H), 6.96(m, 10H), 6.91(d, J=9.7Hz, 1H), 6.50(d, J=9.7Hz, 1H), 9.25(s, 1H), 4.19(s, 1H), 4.13(s, 1H), 3.69-3.60(m, 2H), 3.20(m, 1H), 1.78(m, 1H), 0.97(d , J=6.4Hz, 3H), 0.86 (d, J=6.4, 3H).

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Abstract

The invention relates to a ferrocene derivative and application thereof. The ferrocene derivative is prepared by combining a 2,3-glyoxalidine-[1,2-a]-pyridine compound with ferrocene and can be used for discomposing chiral secondary alcohol raceme, and when the ferrocene derivative is used for discomposing some specific secondary alcohol substrates, the S value of the ferrocene derivative can be as high as 1119. Besides, the ferrocene derivative provided in the invention is easy to separate and purify.

Description

technical field [0001] The invention relates to a ferrocene derivative and its use, in particular to a ferrocene derivative with planar chirality and central chirality and its application in the resolution of racemates. Background technique [0002] Since Vejeds et al. reported the first chiral phosphine-catalyzed kinetic resolution of secondary alcohols in 1996, many efficient chiral acyl transfer catalysts, especially chiral phosphines and chiral amines, have been successfully applied to secondary Kinetic resolution of alcohols. In the kinetic resolution of secondary alcohols, Vejeds et al. reported using a bicyclic chiral phosphine catalyst with a maximum S value of 369 (Vedejs, E.; Daugulis, O.J. Am.Chem.Soc.1999, 121, 5813; Vedejs, E.; MacKay, J.A. Org. Lett. 2001, 3, 535). Fu et al. designed and synthesized planar chiral DMAP compounds with the highest S value of 95 (Fu, G.C.; Ruble, J.C.J.Am.Chem.Soc.1997, 119, 1492; Fu, G.C.; Ruble, J.C.J.Org.Chem. 1998, 63, 2794)...

Claims

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Application Information

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IPC IPC(8): C07F17/02B01J31/12C07B57/00C07C33/20C07C29/92C07C27/02C07C33/22C07C43/23C07C41/44C07C205/19C07C201/16C07C33/18C07C33/46
Inventor 邓卫平胡斌孟萌杜文婷
Owner EAST CHINA UNIV OF SCI & TECH
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