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Chiral diol compound, chiral crown ether compound and preparation methods thereof

A technology of chiral diols and compounds, which is applied in the fields of ether preparation, organic chemical method, and alkylene oxide preparation ether, etc.

Active Publication Date: 2020-04-24
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the direct use of asymmetric catalytic method to prepare chiral polyethylene glycol has not been reported

Method used

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  • Chiral diol compound, chiral crown ether compound and preparation methods thereof
  • Chiral diol compound, chiral crown ether compound and preparation methods thereof
  • Chiral diol compound, chiral crown ether compound and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] This embodiment provides a chiral diol compound I, the structural formula of which compound I is as follows:

[0044]

[0045] Among them: R is hydrogen, C 1 -C 20 Alkyl, C 3 -C 16 Cycloalkyl, C 4 -C 16 The heterocyclic group containing N, O or S, C 6 -C 24 The aryl group, the substituent contains N, O, S, P or halogen C 6 -C 24 Substituted aryl, C 6 -C 26 Arylalkyl, -C n h 2n -OR 1 、-C n h 2n -SR 2 or -C n h 2n -NR 3 R 4 One of them; wherein, n is any integer from 1 to 10, R 1 , R 2 , R 3 and R 4 for hydrogen, C 1 -C 8 Alkyl, C 4 -C 15 Aryl or C 5 -C 15 Arylalkyl;

[0046] R' is -CH 2 CH 2 -(X-CH 2 CH 2 ) m -or-CH 2 -Y-CH 2 -; Wherein, X is O, S or N-R 5 ; 5 for the above R 1 One of them; m is any integer from 0-10000; Y is C 1 -C 20 Alkyl, C 3 -C 16 Cycloalkyl, C 4 -C 16 The heterocyclic group containing N, O or S, C 6 -C 24 The aryl group, the substituent contains N, O, S, P or halogen C 6 -C 24 Substituted aryl, ...

Embodiment 2

[0051] This embodiment provides a chiral diol compound I, the structural formula of which compound I is as follows:

[0052]

[0053] Among them: R is hydrogen, C 1 -C 20 Alkyl, C 3 -C 16 Cycloalkyl, C 4 -C 16 The heterocyclic group containing N, O or S, C 6 -C 24 The aryl group, the substituent contains N, O, S, P or halogen C 6 -C 24 Substituted aryl, C 6 -C 26 Arylalkyl, -C n h 2n -OR 1 、-C n h 2n -SR 2 or -C n h 2n -NR 3 R 4 One of them; wherein, n is any integer from 1 to 10, R 1 , R 2 , R 3 and R 4 for hydrogen, C 1 -C 8 Alkyl, C 4 -C 15 Aryl or C 5 -C 15 Arylalkyl;

[0054] R' is -CH 2 CH 2 -(X-CH 2 CH 2 ) m -or-CH 2 -Y-CH 2 -; Wherein, X is O, S or N-R 5 ; 5 for the above R 1 One of them; m is any integer from 0-10000; Y is C 1 -C 20 Alkyl, C 3 -C 16 Cycloalkyl, C 4 -C 16 The heterocyclic group containing N, O or S, C 6 -C 24 The aryl group, the substituent contains N, O, S, P or halogen C 6 -C 24 Substituted aryl, ...

Embodiment 3

[0059] This embodiment provides a chiral diol compound I, the structural formula of which compound I is as follows:

[0060]

[0061] Among them: R is hydrogen, C 1 -C 20 Alkyl, C 3 -C 16 Cycloalkyl, C 4 -C 16 The heterocyclic group containing N, O or S, C 6 -C 24 The aryl group, the substituent contains N, O, S, P or halogen C 6 -C 24 Substituted aryl, C 6 -C 26 Arylalkyl, -C n h 2n -OR 1 、-C n h 2n -SR 2 or -C n h 2n -NR 3 R 4 One of them; wherein, n is any integer from 1 to 10, R 1 , R 2 , R 3 and R 4 for hydrogen, C 1 -C 8 Alkyl, C 4 -C 15 Aryl or C 5 -C 15 Arylalkyl;

[0062] R' is -CH 2 CH 2 -(X-CH 2 CH 2 ) m -or-CH 2 -Y-CH 2 -; Wherein, X is O, S or N-R 5 ; 5 for the above R 1 One of them; m is any integer from 0-10000; Y is C 1 -C 20 Alkyl, C 3 -C 16 Cycloalkyl, C 4 -C 16 The heterocyclic group containing N, O or S, C 6 -C 24 The aryl group, the substituent contains N, O, S, P or halogen C 6 -C 24 Substituted aryl, ...

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Abstract

The invention discloses a chiral diol compound, a chiral crown ether compound and preparation methods thereof. The chiral diol compound and the chiral crown ether compound have tetra-substituted three-dimensional centers, can be widely applied to chiral recognition and chiral separation technologies, and can be used as chiral catalysts and applied to asymmetric catalytic reactions to prepare chiral compounds. According to the preparation method of the compound provided by the invention, racemic 4-substituted-4-vinyl-1,3-dioxolane-2-ketone compounds are used as raw materials and react with diolunder the catalytic action of a palladium complex generated by coordination between a palladium source and a chiral ligand and a boron compound, which are used as catalysts to prepare the chiral diolcompound. The preparation method provided by the invention is a palladium and boron co-catalyzed asymmetric etherification reaction, and has the advantages of high catalytic activity, high regioselectivity, diastereoselectivity and enantioselectivity, mild reaction conditions, and convenient and easily available reaction raw materials.

Description

technical field [0001] The invention relates to compounds in the technical field of chemical engineering and a preparation method thereof, in particular to a chiral diol compound, a chiral crown ether compound and a preparation method thereof. Background technique [0002] Since Cram's pioneering work on chiral crown ethers (Cram, D.J.Am.Chem.Soc.1973,95,2692-2693.), various chiral crown ethers and their derivatives with different chiral units have been Developed successively and widely used in chiral recognition (Wang, C.Chin.J.Org.Chem.2013,33,280-287.), chiral separation technology (Feringa,B.L.Org.Biomol.Chem.2011,9, 36-51.), and phase transfer catalysts, etc. (Sala, G.D. Synthesis 2018, 50, 4777-4795.). It is well known that polyethylene glycol is a useful ligand for organic transformations and polymerizations catalyzed by some alkali metals, alkaline earth metals, or lanthanides (Aspinall, H.C. Chem. Rev. 2002, 102, 1807-1850.), and chiral Polyethylene glycol analogu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/03C07C43/178C07C303/36C07C311/17C07D213/30C07C43/23C07D317/54C07D333/16C07D498/18
CPCC07C41/03C07C43/178C07C303/36C07C311/17C07D213/30C07C43/23C07D317/54C07D333/16C07D498/18C07B2200/07
Inventor 张勇健萨达拉兹赵灿
Owner SHANGHAI JIAO TONG UNIV
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