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Chirality sulfonamide aminol ligand based on prolinol, its preparing method and application

A technology for sulfonamidoamine alcohol and prolinol, which is applied in the field of chiral sulfonamidoamine alcohol ligands, can solve the problems of low overall yield and the like, and achieve the effects of high reaction yield and simple operation

Inactive Publication Date: 2007-08-15
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this way, the overall yield of ligand synthesis in these two documents is low, and most of them need to be purified by column chromatography

Method used

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  • Chirality sulfonamide aminol ligand based on prolinol, its preparing method and application
  • Chirality sulfonamide aminol ligand based on prolinol, its preparing method and application
  • Chirality sulfonamide aminol ligand based on prolinol, its preparing method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Commercially available L-prolinol (3.80mmol, 0.39g) and (R)-2-phenyl-1-tosylcycloethyleneimine (3.66mmol, 1.00g) were dissolved in 30ml of acetonitrile The mixture was kept under reflux for 10 hours, and TLC detection found that the reaction had basically ended. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of dichloromethane and petroleum ether (60-90°C) to obtain a white solid (0.89g), with a yield of 65% and a melting point of 113 -114℃; Specific rotation is [α] D 25 =+1.33(c0.5, CHCl 3 ); NMR data are: 1 H NMR (CDCl 3 ): 1.61-1.69(m, 4H), 2.44(s, 3H), 2.62(d, J=6.8Hz, 1H), 2.87(t, J=8.0 Hz, 2H), 3.03-3.06(m, 2H ), 3.17-3.22(m, 1H), 3.49-3.54(m, 1H), 3.63-3.66(m, 1H), 7.14-7.16(m, 2H), 7.29(t, J=5.2Hz, 5H), 7.68(d, J=8.0Hz, 2H); 13 C NMR (CDCl 3 ): 21.71, 24.51, 29.10, 45.68, 52.77, 61.54, 64.59, 66.56, 127.28, 128.58, 129.01, 129.88, 137.02, 138.94, 143.64; high-resolution mass spectrometry da...

Embodiment 2

[0036] Apply the ligand synthesized in Example 2 to the asymmetric addition reaction of diethylzinc to α-naphthaldehyde, use n-hexane as solvent, stir at room temperature for about 20 hours, and obtain the product with absolute configuration S , the chemical yield is 90%, and the enantioselectivity exceeds 99%.

Embodiment 3

[0038] Apply the ligand synthesized in Example 2 to the asymmetric addition reaction of diethylzinc to o-chlorobenzaldehyde, use n-hexane as solvent, stir at room temperature for about 20 hours, and obtain the product with absolute configuration R , the chemical yield is 92%, and the enantioselectivity exceeds 99%.

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Abstract

The invention discloses a making method and application of chiral sulfonamide amide-alcohol ligand based on proamide-alcohol, which is characterized by the following: adopting L-proamide-alcohol as raw material; making each ligand framework possess 1-3 chiral center; proceeding selectivity loop-opening reaction for cycloethyliminum; improving receiving rate obviously; adopting chiral sulfonamide amide-alcohol ligand and similarity as catalyst ligand in the asymmetrical synthetic reaction; fitting for applying in the asymmetrical diethyl zinc additioning reaction, alkynyl zinc additioning reaction for carbonyl compound, reducing reaction and aldehyde alcohol condensing reaction.

Description

technical field [0001] The present invention relates to a class of optically active prolinol-based chiral sulfonamidoaminoalcohol ligands. [0002] The present invention also relates to the preparation method of the above-mentioned ligand. [0003] The present invention also relates to the use of the aforementioned ligands. Background technique [0004] At present, various types of chiral ligands have been used in the asymmetric addition reaction of diethylzinc to aldehydes and have achieved good results, among which sulfonamide ligands are a relatively good class of ligands, including bis pair Toluenesulfonamides (bissulfonamide), bistrifluoromethanesulfonamides (bistriflamide) and sulfonamide alcohols (sulfonamido alcohol) and the like. But this kind of ligand must be tetraisopropoxytitanium (Ti(O i Pr) 4 ) to obtain better results in asymmetric addition reactions. Furthermore, to date there are very few ligands suitable for both aromatic aldehydes as well as aliphati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09C07C311/05
Inventor 万伯顺毛金成陆世维吴凡
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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