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P-chiral N-vinyl phosphoramide, chiral phosphoramide compound and preparation method of chiral phosphoramide compound

A technology based on phosphonamides and phosphonamides, which is applied in the field of organic synthetic chemistry, can solve problems such as the unreported catalytic methods of chiral phosphonamides, and achieve the effects of great application value, high yield, and mild reaction conditions

Inactive Publication Date: 2021-10-12
NANJING UNIV OF SCI & TECH
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Problems solved by technology

For the synthesis of chiral phosphine compounds, although some progress has been made so far, in previous studies, phosphine compounds were all asymmetrically reacted on C or O atoms to construct chiral phosphine compounds, and phosphine compounds were constructed by There is no report on the catalytic method of preparing chiral phosphonamide compounds by asymmetric reaction

Method used

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  • P-chiral N-vinyl phosphoramide, chiral phosphoramide compound and preparation method of chiral phosphoramide compound
  • P-chiral N-vinyl phosphoramide, chiral phosphoramide compound and preparation method of chiral phosphoramide compound
  • P-chiral N-vinyl phosphoramide, chiral phosphoramide compound and preparation method of chiral phosphoramide compound

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Embodiment

[0047]

[0048] Step 1, the reaction is carried out in a glove box, and under an argon protective atmosphere, [Ir(cod)Cl] is added to a 5ml reaction bottle A equipped with a stirring bar 2 (1.4mg, 2.0mol%), chiral phosphoramide ligand (1.9mg, 4.0mol%), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) (1.4mg , 10.0mol%), reaction solvent toluene (0.5mL), and reacted at 25°C for 30min to generate an orange catalyst pre-stirred solution;

[0049] Step 2, under an argon protective atmosphere, add cinnamyl phosphate (compound 1) (27mg, 1.0eq.), phosphonamide (compound 2) (48mg, 1.5eq.), bis(tri Methylsilyl)potassium amide (KHMDS) (100μL, 1M in THF, 1.0eq.), reaction solvent toluene (0.5mL), and react at 25°C for 48h. After the reaction, the crude product was purified by silica gel column chromatography to obtain P-chiral N-vinylphosphonamide (compound 3), with a yield of 80% and an ee of 91%;

[0050] 1 H NMR (500MHz, Chloroform-d) δ7.61(d, J=8.0Hz, 2H), 7.35–7.34(m, 2H), 7.24(d, J=...

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Abstract

The invention discloses P-chiral N-vinyl phosphoramide, a chiral phosphoramide compound and a preparation method of the chiral phosphoramide compound. The method is based on an asymmetric allyl substituted isomerization strategy, cinnamyl phosphate and phosphoramide are used as raw materials, [Ir (cod) Cl] 2 is used as a catalyst, chiral phosphoramide is used as a ligand, toluene is used as a solvent, enantiomer-enriched N-vinyl phosphoramide molecules are efficiently obtained, and the P-chiral N-vinyl phosphoramide molecules are further synthesized and converted to obtain the chiral phosphoramide compound. The method disclosed by the invention is mild in reaction condition, simple, convenient and feasible, the raw materials are stable and easy to obtain, the enantioselectivity and yield of the product are relatively high, and the obtained P-chiral N-vinyl phosphonamide and chiral phosphonamide compound can be used as a catalyst for various asymmetric catalytic reactions.

Description

technical field [0001] The invention relates to a P-chiral N-vinyl phosphonamide, a chiral phosphonamide compound and a preparation method thereof, belonging to the technical field of organic synthesis chemistry. Background technique [0002] Enantiomerically enriched chiral phosphine compounds are widely used in the fields of biochemistry, medicinal chemistry, and asymmetric organic synthesis. In particular, nitrogen phosphine compounds have been increasingly favored by the pharmaceutical industry, such as phosphonamidated drugs Sofosbuvir, the marketed drug tenofovir alafenamide (TAF), and a drug that has shown some value in the treatment of new coronavirus infections-remdesivir. Therefore, it is necessary to develop efficient methods for the synthesis of chiral nitrogen phosphine compounds. [0003] At present, the preparation methods of chiral phosphine compounds mainly include desymmetrization of prochiral phosphine compounds, kinetic resolution of racemic phosphine co...

Claims

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Application Information

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IPC IPC(8): C07F9/44C07F9/6574B01J31/02
CPCC07F9/448C07F9/65744B01J31/0267B01J31/0264B01J31/0271C07B2200/07
Inventor 何英张秀莲闵小龙易文斌
Owner NANJING UNIV OF SCI & TECH
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