Method for stereoselective synthesis of (E)-trisubstituted olefin
A stereoselective, three-substitution technology, which is applied in the preparation of halogenated hydrocarbons, organic chemical methods, chemical instruments and methods, etc., can solve the problems of expensive catalyst, large amount of catalyst, and long reaction time, etc., and achieve high industrial application prospects, Great practical application value, high stereoselective effect
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Embodiment 1
[0043] Embodiment 1: Synthesis of E-trisubstituted olefins by catalytic isomerization
[0044]
[0045] Reaction operation: at 25°C, add CoCl to a dry reaction test tube 2 (0.01mmol), PAO ligand (0.01mmol), alkene (10mmol), toluene (1mL), injected into triethylsodium borohydride (0.03mmol), then stirred at room temperature for 10 minutes and separated by column chromatography to obtain the product .
[0046] Product 1: (E)-1-(But-2-en-2-yl)-4-methoxybenzene
[0047]
[0048] Colorless oily liquid, yield>99%, E / Z>99 / 1. 1 H NMR: (400.0MHz, CDCl 3 )δ7.33-7.28(m,2H),6.87-6.82(m,2H),5.83-5.73(m,1H),3.80(s,3H),2.03-1.98(m,3H),1.78(dq, J=6.8,1.2Hz,3H).
[0049] Product 2: (E)-1-(But-2-en-2-yl)-3-methoxybenzene.
[0050]
[0051] Colorless oily liquid, yield>99%, E / Z>99 / 1. 1 H NMR: (400.0MHz, CDCl 3 )δ7.22(t, J=7.8Hz, 1H), 6.97(d, J=7.8Hz, 1H), 6.93-6.89(m, 1H), 6.79-6.74(m, 1H), 5.91-5.83(m ,1H),3.81(s,3H),2.01(s,3H),1.79(dq,J=6.8,1.0Hz,3H).13C NMR:(100.6MHz,CDCl3)d...
Embodiment 2
[0115] Embodiment 2: the asymmetric epoxidation reaction comparison of three substituted alkenes
[0116]
[0117] Reaction operation: at room temperature, in a dry reaction test tube, add Salen-Mn catalyst (0.05mmol), olefin (1mmol), dichloromethane (DCM) (2mL), sodium hypochlorite (NaOCl) (1.5mmol), then After stirring for 3 hours at °C, the product was isolated by column chromatography.
[0118] The reaction using the E / Z-trisubstituted olefin mixture (E / Z=20 / 80) as the raw material gives the mixed product of the epoxidation reaction in a ratio of 1:4. The reaction starting from E-trisubstituted alkenes (E / Z>99 / 1) gave product 24.
[0119] Product 24: (2S,3S)-2,3-dimethyl-2-phenyloxirane
[0120]
[0121] Colorless oily liquid, yield 82%, 93% ee. 1 HNMR: (400.0MHz, CDCl 3 )δ7.20-7.37 (m, 5H), 2.97 (q, J = 5.6Hz, 1H), 1.69 (s, 3H), 1.45 (d, J = 5.4Hz, 3H); 13 C NMR (100MHz, CDCl 3 )δ: 143.5, 128.7, 127.6, 125.4, 62.9, 60.6, 17.8, 14.9.
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