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Chiral zinc complex and copper complexes of alpha-phenylethylamine

A technology of zinc phenylethylamine acetate and chirality, which is applied to the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, compounds of Group 4/14 elements of the periodic table, etc., and can solve complex operations, low efficiency

Inactive Publication Date: 2011-05-25
罗梅
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0029] Chiral cyanohydrin can be separated from the racemate, but the operation is complicated and the efficiency is low

Method used

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  • Chiral zinc complex and copper complexes of alpha-phenylethylamine
  • Chiral zinc complex and copper complexes of alpha-phenylethylamine
  • Chiral zinc complex and copper complexes of alpha-phenylethylamine

Examples

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Embodiment Construction

[0075] (1) Examples of preparation of chiral complexes

[0076] 1, 1a: Synthesis of chiral (S)-α-phenylethylamine zinc acetate metal-organic complexes

[0077] Weigh 2.191g Zn(CH 3 COO) 2 2H 2 Add O (0.01mol) into a 100mL round-bottomed flask, add 25mL tetrahydrofuran as a solvent, add a stirrer, measure 2.7mL α-phenylethylamine (0.02mol) with a syringe under stirring, add it to the flask, Put on the condensing tube, connect to tap water, place on a magnetic heating stirrer and heat to reflux for 24 hours, remove the solvent with a rotary evaporator, and recrystallize with petroleum ether to obtain colorless crystals with a yield of 90%.

[0078] 1 HNMR (500MHz, CDCl 3 )7.22~7.31(m, 10H), 4.06~4.07(d, J=6.5Hz, 1H), 3.06(br, 1H), 1.94(s, 6H), 1.40~1.42(d, J=6.5Hz, 6H ). 13 C NMR (75MHz, CDCl 3 )179.70, 144.04, 128.94, 127.92, 125.92, 51.82, 23.94, 23.10. IR (KBr) cm -1 : 3130, 1620, 1390, 1170, 702.

[0079] 2. 1b: Synthesis of chiral (S)-α-phenylethylamine acetate co...

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Abstract

The invention relates to a chiral zinc acetate complex of alpha-phenylethylamine, a chiral copper acetate complex of alpha-phenylethylamine and a chiral copper chloride complex of alpha-phenylethylamine which are used as catalyst. When the complexes are used in the nitrile silicification reactions of aromatic aldehydes such as benzaldehyde, 2-fluorobenzaldehyde, 2-methoxybenzaldehyde, 2-methylbenzaldehyde, 4-methylbenzaldehyde, 4-methoxybenzaldehyde, 4-fluorobenzaldehyde, 4-chlorobenzaldehyde and 4-bromobenzaldehyde to prepare chiral target products, the chiral catalysts have good catalytic activities and high enantioselectivity in the nitrile silicification reactions.

Description

1. Technical field [0001] The invention relates to a new application of a metal-organic coordination compound (complex), specifically a new application of a zinc-nitrogen and copper-nitrogen complex of α-phenylethylamine in an asymmetric catalytic reaction. 2. Background technology [0002] Metal-organic complexes of zinc-nitrogen and copper-nitrogen have some excellent catalytic properties, which are closely related to materials science, organic synthesis, life science and other disciplines. The field of asymmetric catalysis is of great interest. It has become one of the research hotspots at home and abroad, and there have been a large number of literature reports (1-17). [0003] (1) Guillarme, S.; Whiting, A. Synlett. 2004, 4, 711. [0004] (2) Pickin, Kerry A.; Kindy, Jennifer M.; Day, Cynthia S.; Welker, Mark E.J. Organomet. Chem. 2003, 681, 120. [0005] (3) Bayer, A.; Gautun, Odd R. Tetrahedron: Asymmetry 2001, 12, 2937. [0006] (4) Lee, Y.M.; Li, B. Hoveyda, A.H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07F7/18C07C253/00C07C255/36C07C255/37
Inventor 罗梅
Owner 罗梅
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