Chiral catalyst in binaphthol synthesis technology

A technology of chiral catalyst and synthesis process, which is applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, organic compound preparation, etc. Industrial applicability, affecting product performance and other issues, to achieve the effect of simplifying recycling steps, low cost, and improving feasibility

A technology of chiral catalyst and synthesis process, which is applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, organic compound preparation, etc. Industrial applicability, affecting product performance and other issues, to achieve the effect of simplifying recycling steps, low cost, and improving feasibility

CN103480418AActive Publication Date: 2014-01-01宿迁思睿屹新材料股份有限公司
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  • Chiral catalyst in binaphthol synthesis technology
  • Chiral catalyst in binaphthol synthesis technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] This example provides a preparation method of a chiral catalyst, which is realized through the following steps: dissolve 5.0g (1R,2R)1,2-cyclohexanediamine in 50mL of chloroform, ice bath, and then slowly drop 15.0g3-hydroxyl-2-naphthone, after reacting 12 hours, purify with silica gel column (mobile phase is : =1:1.5), to obtain 15.64g of yellow solid, dissolve the solid in 200mL of methanol, add 7.5g of ferric chloride, stir at room temperature for 3 hours, spin off the solvent, and recrystallize with n-hexane to obtain 19.14g of chiral catalyst a .

Embodiment 2

[0039] This example provides a preparation method of a chiral catalyst, which is realized through the following steps: dissolve 5.5g (1R,2R)1,2-cyclohexanediamine in 50mL of chloroform, ice-bath, and then slowly drop 18.0g3-hydroxyl-2-naphthone, after reacting for 18 hours, purify with silica gel column (mobile phase is : =1:1.5), to obtain 16.85 g of yellow solid, dissolve the solid in 250 mL of methanol, add 8.5 g of ferric chloride, stir at room temperature for 4.5 hours, spin off the solvent, and recrystallize with n-hexane to obtain 20.25 g of chiral catalyst b .

Embodiment 3

[0041] This example provides a preparation method of a chiral catalyst, which is realized by the following steps: dissolve 4.5g (1S,2S)1,2-cyclohexanediamine in 50mL of chloroform, ice-bath, and then slowly drop 14.0g3-hydroxyl-2-naphthone, reacted after 10 hours, purified with silica gel column (mobile phase is : =1:1.5), to obtain 13.57g of yellow solid, dissolve the solid in 180mL of methanol, add 7.0g of ferric chloride, stir at room temperature for 3 hours, spin off the solvent, and recrystallize with n-hexane to obtain 17.02g of chiral catalyst c .

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Abstract

A chiral catalyst in a binaphthol synthesis technology is a 1,2-cyclohexanediamino-2-(3-hydroxy-2-naphthalenone)Schiff base-ferric iron complex, and the 1,2-cyclohexanediamino-2-(3-hydroxy-2-naphthalenone)Schiff base is generated through reacting (1R,2R) or (1S,2S)1,2-cyclohexanediamine with 3-hydroxy-2-naphthalenone. The structural formula of the chiral catalyst is shown in the specification. Cheap ferric iron same with the center ligand of the catalyst is adopted as an oxidant to carry out a chiral catalytic reaction, and the adoption metal ions as an oxidant can guarantee the high conversion rate of a product; the catalyst does not react with the oxidant to form impurities in a catalyst and oxidant recovery process, so a recovery step is simplified, and the recovery feasibility of the catalyst is improved; and the recycle of the catalyst and the oxidant can guarantee a high optical purity of the product, a high conversation rate and a high optical purity can be realized on the basis of a low cost, the pressure to the environmental protection is reduced, and the green chemistry is realized.

Description

technical field [0001] The invention relates to the field of asymmetric catalytic synthesis, in particular to a chiral catalyst in the binaphthol synthesis process. Background technique [0002] In organic chemistry, some compounds have the same molecular weight and the same molecular structure, but the left and right arrangements are opposite, just like the real object and its mirror image, and like two hands that cannot overlap each other, so these compounds are called chiral compounds. A chiral compound must have optical activity, and the racemate of an optically active chiral compound has two enantiomers. This enantiomer is formed by mixing optical isomers with opposite optical rotation directions and the same optical rotation ability. The optical activity of the racemate cancels each other due to the interaction between the optical isomers, so the racemate is not optically active. [0003] The chirality of the compound determines that the compound has some physical pr...

Claims

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Application Information

Patent Timeline
01 Jan 2014
Publication
CN103480418A
IPC
B01J31/22; C07F15/02; C07C39/14; C07C37/16
CPC
Y02P20/584
Inventors
陈艳珍; 孙隹悦