A kind of chiral phosphine-containing ligand and hydrogen bond donor and preparation method and application thereof
A technology of hydrogen bond donors and ligands, which is applied in the field of chiral phosphine-containing and hydrogen bond donor ligands and their preparation and application, and can solve the problems of no chiral catalysis
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preparation example 1
[0033]
[0034]Take compound 7 (1.95g, 5.28mmol), compound 8 (1.62g, 5.28mmol), EDCI (1.21g, 6.31mmol), DMAP (64mg, 0.528mmol) in a 100mL round bottom flask, add a stirring bar, and replace Nitrogen three times, add dry dichloromethane, take triethylamine (1.068g, 10.56mmol) in the reaction liquid, react at room temperature, TLC monitoring. After the reaction was complete, the reaction was quenched with saturated brine, extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate=3 / 1) Ligand L1 was obtained as a white foamy solid (2.26 g, yield = 65%). Compound 7 was prepared according to literature (F. Sébastien, B. Valérie, J.P. Lepoittevin, Eur. J. Org. Chem. 2007, (7), 1145-1152).
[0035] 1 H NMR (400MHz, CDCl 3 )δ8.39(s,1H),7.51(s,2H),7.49–7.46(m,1H),7.32–7.29(m,5H),7.25–7.20(m,3H),7.1...
preparation example 2
[0038]
[0039] Weigh compound 9 (1.2g, 2.99mmol) in a 50mL round bottom flask, add a stirrer, pump out nitrogen, add dry methylene chloride, weigh p-toluene isothiocyanate (477mg, 3.58mmol), slowly Add dropwise to the reaction solution, stir at room temperature, and monitor the reaction by TLC. After the reaction was complete, the reaction solution was directly concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate=2 / 1) to obtain the white foamy solid compound ligand L2 (1.53 g, yield=96%) . Compound 9 was prepared according to the literature (D.S.Huang, X.Q.Liu, L.J.Li, Y.D.Cai, W.G.Liu, Y.Shi, J.Am.Chem.Soc. 2013, 135(22), 8101-8104).
[0040] 1 H NMR (400MHz, CDCl 3 )δ7.46(s,1H),7.35–7.25(m,7H),7.23–7.13(m,5H),6.92–6.84(m,6H),6.77(d,J=6.68Hz,1H),6.06 (d,J=6.80Hz,1H),3.65–3.61(m,2H),2.22(s,3H),2.04(d,J=11.68Hz,1H),1.74–1.65(m,3H),1.30– 1.17(m,3H),1.04–0.96(m,1H)ppm;
[0041] HRMS(m / ...
preparation example 3
[0043]
[0044] Take compound 9 (1g, 2.49mmol) in a 50mL round-bottomed flask, add a stirrer, pump nitrogen, add 20mL of dry dichloromethane, add compound 11 (0.81g, 2.99mmol), stir at room temperature, and monitor by TLC. After the reaction was complete, the reaction was quenched by adding saturated brine, extracted with ethyl acetate (20mL x 3), the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the crude product was subjected to silica gel column chromatography (petroleum ether / acetic acid Ethyl ester=5 / 1) purified to give white foamy solid ligand L3 (1.49g, yield=89%)
[0045] 1 H NMR (400MHz, CDCl 3 )δ9.44(s,1H),8.32(d,J=9.20Hz,1H),7.81(s,2H),7.64–7.61(m,1H),7.52(s,1H),7.32–7.18(m ,10H),7.10(t,J=7.72Hz,2H),6.92(d,J=8.76Hz,1H),6.83(t,J=6.16Hz,1H),4.67–4.60(m,1H),3.73 –3.70(m,1H),2.22(d,J=11.00Hz,1H),1.83(d,J=11.16Hz,1H),1.73(d,J=13.24Hz,1H),1.38–1.31(m, 2H),1.28–1.10(m,2H),1.06–0.95(m,1H)ppm;
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