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Polycarbonyl-substituted chiral pyrrolidine derivative and preparation method thereof

A technology of derivatives and pyrrolidine, which is applied in the field of polycarbonyl functionally substituted chiral pyrrolidine derivatives and its preparation, can solve the problem of high enantioselectivity and few synthetic methods of polycarbonyl functionally substituted chiral pyrrolidine derivatives, etc. problem, to achieve the effect of high enantioselectivity, considerable application value, and simple reaction operation

Inactive Publication Date: 2018-12-28
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the problem that there are not many synthetic methods for polycarbonyl functional substituted chiral pyrrolidine derivatives, the present invention proposes a polycarbonyl functional substituted chiral pyrrolidine derivative and a preparation method thereof. The synthetic method is simple to operate, the reaction conditions are mild, and the substrate Strong universality, high product yield and high enantioselectivity

Method used

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  • Polycarbonyl-substituted chiral pyrrolidine derivative and preparation method thereof
  • Polycarbonyl-substituted chiral pyrrolidine derivative and preparation method thereof
  • Polycarbonyl-substituted chiral pyrrolidine derivative and preparation method thereof

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Effect test

Embodiment 1

[0030] Under nitrogen atmosphere, (R)-DTBM-SegPhos (13mg, 0.0108mmol, 6mol%), AgOAc (1.6mg, 0.0096mmol, 5mol%) was added to the dissolved chalcone (3.8mg, 0.0182mmol, 10mol%) ) in 2 mL of acetone solution, after pre-stirring for 30 minutes at -40°C, add methyleneamine ylide 1a (0.2mmol) and enone compound 2a (0.182mmol) in sequence, react at -40°C for 12h, and monitor the reaction by TLC , filtered through diatomaceous earth, extracted, the filtrate was concentrated, and purified by silica gel column chromatography to obtain a colorless oily liquid 3a with a yield of 68%. The ee value was measured by chiral high performance liquid chromatography to be 96%.

[0031]

[0032] The physicochemical index of this product: 1 H NMR (400MHz, CDCl 3 )δ7.65(d, J=7.4Hz, 2H), 7.45(t, J=7.4Hz, 1H), 7.38(d, J=6.7Hz, 2H), 7.27(dd, J=11.3, 7.7Hz, 5H), 4.42(dd, J=17.5, 8.1Hz, 2H), 4.34(d, J=8.4Hz, 1H), 4.09(q, J=7.1Hz, 2H), 3.93(t, J=7.9Hz, 1H), 3.79(s, 3H), 2.59(s, 1H), 1.15(t, J=7.1Hz...

Embodiment 2

[0034] The preparation method was the same as in Example 1, and the dissolved chalcone was changed to 8mol% (3.04mg, 0.0146mmol) to obtain a colorless oily liquid 3a with a yield of 58%, and the ee value measured by chiral high-performance liquid chromatography was 95%. .

Embodiment 3

[0036]The preparation method was the same as in Example 1, and the dissolved chalcone was changed to 6mol% (2.28mg, 0.0109mmol) to obtain a colorless oily liquid 3a with a yield of 63%, and the ee value measured by chiral high-performance liquid chromatography was 94%. .

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Abstract

The invention relates to the field of organic chemistry. In order to solve the problem that methods of synthesizing the polycarbonyl-substituted chiral pyrrolidine derivative are not many, the invention provides a polycarbonyl-substituted chiral pyrrolidine derivative and a preparation method thereof. Under the protection of inert gas, a complex formed by a metal-catalyzed precursor and a chiral phosphine ligand is used as a catalyst, and the polycarbonyl-substituted chiral pyrrolidine derivative is synthesized by a [3+2] cycloaddition reaction of ketene and azomethine ylides. The synthetic method is simple to operate, reaction conditions are mild, the substrate universality is high, the product yield is high, the enantioselectivity is high, the synthesized compound is an important nitrogen-containing heterocyclic compound which can be widely applied to various fields of organic synthesis, medicine, material chemistry and fine chemicals.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a polycarbonyl functional substituted chiral pyrrolidine derivative and a preparation method thereof. Background technique [0002] There are many kinds of nitrogen-containing heterocyclic compounds, which are commonly found in drug molecules and natural products. Among them, pyrrolidine is an important class of five-membered nitrogen heterocyclic compounds, which have the characteristics of low ring tension and high stability. Chiral pyrrolidine units are important components of many natural alkaloids and active pharmaceutical molecules. Some drug molecules containing pyrrolidine structure have practical value such as antibiotics, bactericides, additives, etc., which makes them more and more demanded in the market. Therefore, the synthesis of chiral pyrrolidine compounds has attracted widespread attention of organic synthesis workers . Such compounds were initially extracted ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16
CPCC07D207/16C07B2200/07
Inventor 尹官武徐利文李宁徐征郑战江叶飞崔玉明曹建杨雪敏杨科芳
Owner HANGZHOU NORMAL UNIVERSITY
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