Novel chiral nitrogen oxygen ligands and synthesis method thereof
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A chiral, nitrogen-oxygen technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc.
Inactive Publication Date: 2018-05-29
SICHUAN UNIV
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[0012] In summary, based on the existing chiral nitrogen and oxygen, we found that chiral nitrogen and oxygen ligands can be used in Een and aza-Een Reaction, F-C Reaction, Roskamp Reaction, Sulfa-Michael Reaction, MichaelReaction, Oxa-Michael Reaction, Herero-DA Reaction, Haloamination, Henry andaza-Henry Reaction, Hydroxymethylation, Cyanation Reaction, Mannich Reaction, Aldol Reaction, All y lation Reaction, Amination Reaction, α-Chlorination y and photocatalytic reactions, etc. Therefore, it is of great significance to develop new chiral nitrogen-oxygen ligands for asymmetric catalytic reactions and synthesis, and to solve the problem that existing nitrogen-oxygen cannot catalyze reactions.
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Embodiment 1
[0126] Example 1: Synthesis of Compound L from Compound 2a 4 -RaR
[0127] Add 2,5-dimethoxytetrahydrofuran (1eq) into the reaction vessel, add a small amount of dilute hydrochloric acid, raise the temperature, and hydrolyze it into succinic dialdehyde. Dissolve the succinic dialdehyde obtained above in 1,2-dichloroethane, then add compound 2a (2eq), mix and stir for 15min, continue to add sodium triacetoxyborohydride (2.4eq), stir at room temperature for 12h, slowly add Saturated sodium bicarbonate until no bubbles are generated, extracted and separated with dichloromethane, purified by vacuum distillation column chromatography, and obtained a white solid product. After that, 2b was dissolved in dichloromethane, cooled to -20°C, and m-chloroperoxy Benzoic acid (2.2eq), after stirring for 30min, warm up to room temperature, add saturated sodium bicarbonate, stir for 5 minutes, add dichloromethane for extraction and separation, vacuum distillation column chromatography (ethyl ...
Embodiment 2
[0128] Example 2: Synthesis of Compound L from Compound 2a 6 -RaR
[0129] Add 1,2-cyclohexanediol (1eq) into the reaction vessel, add solvent 1,2-dichloroethane, cool at 0°C, slowly add sodium periodate (2eq) and sodium bicarbonate (2.1eq), Stir at room temperature for 24h, filter, wash with a small amount of solvent, add the obtained filtrate to the stirrer, then add compound 2a (2eq), after stirring for 15min, continue to add sodium triacetoxyborohydride (2.4eq), stir at room temperature for 12h, slowly add Saturated with sodium bicarbonate until no bubbles were generated, extracted and separated with dichloromethane, and purified by column chromatography under reduced pressure to obtain the white solid product 2c. Follow-up operation is referring to embodiment 1.
Embodiment 3
[0130] Example 3: Synthesis of Compound L from Compound 2a 7 -RaR
[0131] Add compound 2a (2eq) to the reaction vessel, add the solvent acetonitrile to dissolve, add 1,7-dibromoheptane (1eq), add diisopropylethylamine (4eq) and sodium iodide (0.2eq), heat Reflux at 100° C. for 12 h, cool to room temperature and suction filter, and conduct vacuum distillation column chromatography of the obtained filtrate (ethyl acetate:petroleum ether=1:1) to obtain the white solid product 2d. Follow-up operation is referring to embodiment 1.
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Abstract
The invention discloses a series of novel chiral nitrogen oxygen ligands and a synthesis method thereof. According to the invention, simple amino acids, amino acid derivatives proline and Leimi acid,4-aminobutyric acid and tetrahydroisoquiline acid are adopted as raw materials, and a series of key processes are adopted, so that 4-carbon, 6-carbon, 7-carbon and 8-carbon novel chiral nitrogen oxygen ligands, 2-A-propane 3-carbon novel chiral nitrogen oxygen ligands, 2,2-di(B)-propane 3-carbon novel chiral nitrogen oxygen ligands, 1,1-dimethyl cyclopropane 3-carbon novel chiral nitrogen oxygen ligands, 1,1-dimethyl cyclobutane 3-carbon novel chiral nitrogen oxygen ligands, 1,1-dimethyl cyclopentane 3-carbon novel chiral nitrogen oxygen ligands and 1,1-dimethyl cyclohexane 3-carbon novel chiral nitrogen oxygen ligands, p-xylene and m-xylene and o-xylene novel chiral nitrogen oxygen ligands, and p-diethylbenzene, m-diethylbenzene and o-diethylbenzene novel chiral nitrogen oxygen ligands, and other novel chiral nitrogen oxygen ligands are finally synthesized. The above novel chiral nitrogen oxygen molecules can realize high enantioselectivity and high reaction activity in a variety of asymmetric reactions, and have great significance in solving reactions which cannot be completed by existing nitrogen oxygen ligands.
Description
technical field [0001] The invention relates to chiral nitrogen-oxygen ligands used as catalysts in asymmetric catalytic reactions and a preparation method thereof, in particular to simple amino acids and amino acid derivatives proline, remic acid, pipecolic acid and tetrahydroisoquinoline Acid as raw material, through a series of key processes, finally synthesized 4 carbon new chiral nitrogen oxygen, 6 carbon new chiral nitrogen oxygen, 7 carbon new chiral nitrogen oxygen, 8 carbon new chiral nitrogen oxygen, 2-A-propane 3-carbon chiral nitrogen oxide, 2,2-diB-propane 3-carbon chiral nitrogen oxide, 1,1-bis-methylcyclopropane 3-carbon chiral nitrogen oxide, 1,1-bis-methylcyclobutane 3-carbon novel chiral nitrogen oxide, 1,1-bis-methylcyclopentane 3-carbon chiral nitrogen oxide, 1,1-bis-methylcyclohexyl New chiral nitrogen oxides with 3 carbons in alkane, p-xylene, m-xylene and o-xylene and aryl substitution new chiral nitrogen oxides, p-diethylbenzene, m-diethylbenzene and o...
Claims
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