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Axial chiral naphthalene-indole phosphine catalyst as well as preparation method and application thereof

A technology of indoles and catalysts, applied in the field of axial chiral naphthalene-indole phosphine catalysts and their preparation, and axial chiral biaryl phosphine compounds, can solve the problems of high synthesis cost, achieve large steric hindrance, reduce Cost, the effect of enhancing the catalytic effect

Active Publication Date: 2021-03-26
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing catalysts of this type are all pure axial chiral framework catalysts, and they are all realized by catalytic asymmetric synthesis strategy, and the synthesis cost is relatively high.

Method used

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  • Axial chiral naphthalene-indole phosphine catalyst as well as preparation method and application thereof
  • Axial chiral naphthalene-indole phosphine catalyst as well as preparation method and application thereof
  • Axial chiral naphthalene-indole phosphine catalyst as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Prepare the axial chiral indole-naphthalene phosphine catalyst as follows:

[0042]

[0043] Prepare the axial chiral indole-naphthalene phosphine catalyst as follows:

[0044] (1) Add 0.5 mmol of formula 1 compound, 0.05 mmol of 4-dimethylaminopyridine, 0.6 mmol of formula 2 compound, 1 mmol of diisopropylethylamine in 5 milliliters of anhydrous dichloromethane, stir at room temperature for 12 Hour. TLC traced the reaction to the end, added 2mL of 1N hydrochloric acid to quench, and then extracted 3 times with 15mL of ethyl acetate, combined the organic phases and dried them with a sufficient amount of anhydrous sodium sulfate, filtered, concentrated, and separated by silica gel column chromatography Purify to obtain compounds of formula 3 and formula 4.

[0045] The structural characterization data of the compound of formula 3 are as follows:

[0046] yield:35%(116.0mg); dr>95:5; white solid; m.p.92.2-92.7℃; [α] D 20 =+32.9(c 0.47, Acetone); 1 H NMR (400MHz, ...

Embodiment 11

[0068]

[0069] Add 0.1 mmol o-methylene quinone compound 14, 0.2 mmol MBH ester compound 15, and 0.02 mmol axial chiral indole-naphthalene phosphine catalyst 13a to 1 ml of chloroform, and react at 35°C for 12 hours. After the reaction was tracked by TLC to the end, after washing and concentration, the compound of formula 16 was obtained by separation and purification through silica gel column chromatography.

[0070] The structural characterization data of the compound of formula 16 are as follows:

[0071] Yield: 92% (39.2mg); colorless oil; 1 H NMR (400MHz, CDCl 3 )δ(ppm):7.44–7.27(m,9H),7.26–7.16(m,1H),6.58(s,1H),6.48(s,1H),6.43–6.36(m,2H),6.33–6.23 (m,1H),5.94(s,1H),5.91(d,J=1.6Hz,2H),5.34(d,J=6.0Hz,1H),5.22(s,2H),4.06–3.84(m, 1H); 13 C NMR (100MHz, CDCl 3)δ (ppm): 165.2, 153.7, 147.9, 142.0, 139.1, 136.7, 135.4, 131.4, 129.8, 128.6, 128.5, 128.3, 127.5, 126.4, 126.1, 119.1, 105.4, 101.3, 93.0, 87.0, IR(KBr):3488,3027,2893,1721,1473,1276,1261,1143,1038,826,750,6...

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Abstract

The invention discloses an axial chiral naphthalene-indole phosphine catalyst as well as a preparation method and application thereof. The chemical structures of the catalyst are represented by formulas 12 and 13, the catalyst has both an axial chiral styrene skeleton and a chiral tertiary amine skeleton, and has relatively large steric hindrance, so that the catalytic effect is enhanced. The preparation method of the axial chiral naphthalene-indole phosphine catalyst is realized by using a cheap chiral reagent resolution strategy, the reaction conditions are mild, the cost is reduced, and thepreparation method is suitable for industrial large-scale production. According to the application of the axial chiral naphthalene-indole phosphine catalyst, the catalyst is applied to asymmetric [4+1] cyclization reaction, so that the catalytic activity is improved, and the stereoselectivity control capability is enhanced.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry and relates to an axial chiral biaryl phosphine compound, in particular to an axial chiral naphthalene-indole phosphine catalyst and a preparation method and application thereof. Background technique [0002] Axial chiral indole-naphthalene compounds can be used as small organic molecule catalysts to catalyze organic chemical reactions. For example, the document Angew.Chem.Int.Ed.2017,56,116 reported that this type of compound can be used as an organophosphine catalyst to catalyze the asymmetric [3+2] cyclization reaction of allenes and imines; document J.Org.Chem.2018 , 83, 10060 reported that this type of compound can be used as an organophosphine catalyst to catalyze the [4+1] cyclization reaction of o-methylenebenzoquinone and Morita-Baylis-Hillman ester; the literature Chem.Sci.2019, 10, 6777 reported Such compounds can be used as chiral phosphine ligands to catalyze the asymmetric...

Claims

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Application Information

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IPC IPC(8): C07F9/572B01J31/02C07D493/04
CPCC07F9/5728B01J31/0267C07D493/04C07B2200/07B01J2231/34Y02P20/584
Inventor 石枫张宇辰谭伟伍平蒋飞
Owner XUZHOU NORMAL UNIVERSITY
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