Synthetic method of (S,S)-salenCo(II) catalyst and application thereof in split of end epoxide compound

Abstract

The invention relates to a synthetic method of a (S,S)-salenCo(II) catalyst and application of the (S,S)-salenCo(II) catalyst in split of an end epoxide compound. The filtrate of the intermediate (R,R)-cyclohexanediamine single salt of a (R,R)-salenCo(II) catalyst is used for synthesizing the (S,S)-cyclohexanediamine single salt; and the (S,S)-cyclohexanediamine single salt is further reacted with 3,5-di-tert-butyl salicylaldehyde and cobalt acetate in a single solvent so as to obtain the (S,S)-salenCo(II) catalyst. With the adoption of the method, the waste, i.e. the intermediate (R,R)-single salt of the (R,R)-salenCo(II) catalyst, is changed into wealth; the single solvent is used; the process is simple; the reaction step is short; the yield is high, the industrialization is easy to achieve; the synthesized (S,S)-salenCo(II) catalyst is activated into a (S,S)-salenCo(III) catalyst with catalytic activation by using air directly in the end epoxide compound; the mode of the (S,S)-salenCo(III) catalyst is synthesized by using the (S,S)-salenCo(II) catalyst is avoided; the splitting effect is the same as that of the method in which the (S,S)-salenCo(III) catalyst is used directly; and the obtained chirality end epoxide compound of which the e value is 99%e is obtained.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, in particular to a synthesis method of (S,S)-salen Co(II) catalyst and its application in splitting terminal epoxy compounds. Background technique [0002] Salen is the abbreviation of N,N-bis(salicylidine)ethylene-diamine[N,N'-ethylene bis(salicylidene imine)], which refers to the general name of diimine compounds, which is the asymmetric catalytic reaction in recent years. And one of the important ligands in asymmetric synthesis. One of its important applications is the hydrolysis kinetic resolution of terminal epoxy compounds (HKR) catalyzed by chiral salen Co complexes. More importantly, as an asymmetric catalyst, chiral salen Co has good and broad application prospects not only in the field of scientific research, but also in technology and industrial production. [0003] The chiral salen Co(II) reported by Jacobsen's group has no catalytic activity, and the chiral salen Co(III) ...

AI Technical Summary

Problems solved by technology

The process has many reaction steps, the mixed solvent used is not conducive to recycling, and the used toluene has a relatively high toxicity. If the water washing is not sufficient in the third step, the inorganic salt content in the catalyst will be obtained at last, thereby affecting the use effect of the catalyst; the fifth step step oxidation yield is low and less than 70%; thus it is unfavorable for suitability for industrialized production

[0005] At the same time, in the first step of the separation reaction using tartaric acid, the filtrate contains another enantiomer; at present, there is no way to effectively use it, and the filtrate can only be treated as waste liquid, polluting the environment

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