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C2-symmetrical bis ruthenium Diphosphine Ligand only with surface chirality

A bisphosphine ligand and chirality technology, which is applied in the ligand field of the chemical technology field, can solve the problems such as the same or similar literature reports that have not been found, and achieve the effects of high reactivity, stereoselectivity, and good application prospects.

Inactive Publication Date: 2008-05-21
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Found through literature search to prior art, have not found the same or similar literature report as the subject of the present invention so far

Method used

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  • C2-symmetrical bis ruthenium Diphosphine Ligand only with surface chirality
  • C2-symmetrical bis ruthenium Diphosphine Ligand only with surface chirality

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 1, the preparation of amide ester (2)

[0016] (S)-(S)-1,1'-bis(diphenylphosphino)-2,2'-bis[(S)-4-isopropyloxazolinyl]ruthenocene (1.65g, 2mmol) was dissolved in tetrahydrofuran (40mL), then water (2mL), trifluoroacetic acid (3.8mL, 49.4mmol), anhydrous sodium sulfate Na 2 SO 4 (18.8g), the suspension was stirred overnight at room temperature, filtered, the solvent was evaporated, the residue was dissolved in dichloromethane (40mL) and then pyridine (7.2mL, 89mmol) and acetic anhydride (12.0mL, 76.4mmol) were added successively, and stirred at room temperature Overnight, the mixture was diluted with dichloromethane (80 mL), washed with dilute hydrochloric acid (10%), water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 1.65 g of the target product, y=82.8%.

[0017] 1 H NMR (400MHz, CDCl 3 ): δ7.34-7.14 (m, 20H, ArH), 6.59-6.58 (brs, 2H, NH), 5.39 (brs, 2H, RcH), 4.83 (brs, 2H, RcH), 4.39-4.34 (dd, J=4Hz, 15.6...

Embodiment 2

[0022] 1, the preparation of amide ester (2)

[0023] (S)-(S)-1,1'-bis(diphenylphosphino)-2,2'-bis[(S)-4-isopropyloxazolinyl]ruthenocene (1.65g, 2mmol) was dissolved in tetrahydrofuran (40mL), then water (2mL), trifluoroacetic acid (3.8mL, 49.4mmol), anhydrous sodium sulfate Na 2 SO 4 (18.8g), the suspension was stirred overnight at room temperature, filtered, the solvent was evaporated, the residue was dissolved in dichloromethane (40mL) and then pyridine (7.2mL, 89mmol) and acetic anhydride (12.0mL, 76.4mmol) were added successively, and stirred at room temperature Overnight, the mixture was diluted with dichloromethane (80 mL), washed with dilute hydrochloric acid (10%), water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 1.65 g of the target product, y=82.8%.

[0024] 1 H NMR (400MHz, CDCl 3 ): δ7.34-7.14 (m, 20H, ArH), 6.59-6.58 (brs, 2H, NH), 5.39 (brs, 2H, RcH), 4.83 (brs, 2H, RcH), 4.39-4.34 (dd, J=4Hz, 15.6...

Embodiment 3

[0029] 1, the preparation of amide ester (2)

[0030] (S)-(S)-1,1'-bis(diphenylphosphino)-2,2'-bis[(S)-4-isopropyloxazolinyl]ruthenocene (1.65g, 2mmol) was dissolved in tetrahydrofuran (40mL), then water (2mL), trifluoroacetic acid (3.8mL, 49.4mmol), anhydrous sodium sulfate Na 2 SO 4(18.8g), the suspension was stirred overnight at room temperature, filtered, the solvent was evaporated, the residue was dissolved in dichloromethane (40mL) and then pyridine (7.2mL, 89mmol) and acetic anhydride (12.0mL, 76.4mmol) were added successively, and stirred at room temperature Overnight, the mixture was diluted with dichloromethane (80 mL), washed with dilute hydrochloric acid (10%), water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 1.65 g of the target product, y=82.8%.

[0031] 1 H NMR (400MHz, CDCl 3 ): δ7.34-7.14 (m, 20H, ArH), 6.59-6.58 (brs, 2H, NH), 5.39 (brs, 2H, RcH), 4.83 (brs, 2H, RcH), 4.39-4.34 (dd, J=4Hz, 15.6,...

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Abstract

The invention relates the synthesis of C2-bis ruthenium doublephosphine ligand. The ligand can be used in metallic catalysis asymmetric reaction, and the ligand has the good reaction active and stereoselectivity. The R is -Me, -Et.

Description

technical field [0001] The invention relates to a ligand in the technical field of chemical industry, specifically a C 2 -Symmetrical only chiral pyridine bisphosphine ligands. technical background [0002] The rapid rise of the chiral drug industry is mainly due to the great development of asymmetric synthesis methodology research, and in turn, the chiral drug industry has promoted the research of asymmetric synthesis methodology. Asymmetric catalytic organic synthesis is one of the most effective and beneficial methods to obtain chiral compounds. In asymmetric catalytic organic synthesis, the key to high reactivity and high enantioselectivity lies in the structure of chiral phosphine ligands. Therefore, the development of chiral phosphine ligands has always been a key research area of ​​concern in academia and industry. [0003] In 1996, Zhang Wanbin and Ikeda Isao's group synthesized for the first time only the chiral C 2 -Symmetrical ferrocene P,P-ligand, and success...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02C07F9/50B01J31/24
Inventor 张万斌谢芳刘德龙罗丽华更红
Owner SHANGHAI JIAOTONG UNIV
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