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Ferrocenyl aza-annulet ligand loaded by tree-like macromolecule as well as synthetic method and application thereof

A technology of dendrimer and ferrocene methylene nitrogen, which is applied in the field of synthesis of ferrocene-based aza small ring ligands, can solve the problem of high cost of catalyst synthesis, and achieves low price, easy modification of price, and method. simple effect

Inactive Publication Date: 2013-05-22
SHANGQIU NORMAL UNIVERSITY
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Problems solved by technology

The work in this area has been studied and reported by some groups, (a) Fan, Q. H.; Liu, G. H.; Chen, X. M. et al. Tetrahedron: Asymmetry , 2001, 12 , 1559-1565. b) Liu, G. H.; Tang, W. J.; Fan, Q. H. Tetrahedron , 2003, 59 , 8603-8611.) However, the supported ligands only achieved moderately high yields and enantioselectivities, and the synthesis cost of the catalyst was relatively high

Method used

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  • Ferrocenyl aza-annulet ligand loaded by tree-like macromolecule as well as synthetic method and application thereof
  • Ferrocenyl aza-annulet ligand loaded by tree-like macromolecule as well as synthetic method and application thereof
  • Ferrocenyl aza-annulet ligand loaded by tree-like macromolecule as well as synthetic method and application thereof

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Embodiment Construction

[0037] compound N - Synthesis of ferrocenemethyleneaziridine di-p-tert-butyldimethylsiloxyphenylmethanol 5:

[0038] Add anhydrous 20 mL THF, 0.53 g (22 mmol) magnesium chips, 5.7 g (20 mmol) p-tert-butyldimethylsilyloxybromobenzene into a 50 mL single-necked flask, add iodine particles and heat to reflux for 2 h. After the reaction is complete, cool to room temperature and add 0.5 g N - Methyl ferrocenemethylaziridine carboxylate. After the completion of the reaction traced by TLC, the reaction was terminated with saturated ammonium chloride. Then extract with ether, combine the organic phases, wash once with saturated NaCl aqueous solution, anhydrous NaCl 2 SO 4 dry. Diethyl ether was distilled off under reduced pressure, and the residue was purified by wet column to obtain 0.95 g (79%) of the product.

[0039] 1 H NMR (400 MHz, CDCl 3 ) δ 7.24 – 7.13 (m, 4H,), 6.78 – 6.70 (m, 4H,), 4.12 – 4.03 (m, 9H,), 3.71 (s, 1H,), 3.51 (d, J = 13.0 Hz, 1H,), 3.22 (d, J =...

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Abstract

The invention provides a ferrocenyl aza-annulet ligand loaded by a Frechet-type tree-like macromolecule as well as a synthetic method and an application thereof in the catalysis asymmetric ethylized reaction of all kinds of aromatic aldehyde. The ligand is prepared by linking chirality ferrocenyl tertiary alcohol to the Frechet-type macromolecule in a manner of covalent bond. The ferrocenyl aza-annulet ligand has the characteristics of simple synthetic method, and high activity and asymmetric selectivity, and is convenient to recycle; and the activity and selectivity of the catalyst are not obviously reduced after three times of recycling.

Description

technical field [0001] The invention relates to a synthetic method and application of a ferrocene-based azaminiature ligand supported by dendrimers. Background technique [0002] The asymmetric nucleophilic addition of metal alkyls to carbonyls with the participation of chiral ligands is one of the most widely studied reactions. The asymmetric addition reaction of dialkylzinc to aldehydes is one of the effective methods for increasing carbon chains and one of the effective methods for preparing chiral alcohols. Since the products of this reaction are important building blocks for pesticides, medicines, fragrances and many natural products, the study of such reactions has been attracting much attention. Such reactions can not only occur under organometallic catalysis, but also under non-organometallic ligands. [0003] Although diethyl zinc was discovered as early as the middle of the 18th century, and its preparation method is relatively mature. However, compared with the...

Claims

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Application Information

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IPC IPC(8): C07F17/02B01J31/22C07B41/02C07C29/40C07C33/20C07D317/54C07C41/30C07C43/23C07C33/18C07C33/46
CPCY02P20/55
Inventor 赵文献刘念李高伟刘澜涛张朋飞赵瑞娟张安安
Owner SHANGQIU NORMAL UNIVERSITY
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