Asymmetric Hydrogenation of Ketones and α,β-Unsaturated Ketones Catalyzed by a Metal-Free Catalyst
An unsaturated and asymmetric technology, applied in asymmetric synthesis, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve problems such as metal residual pollution, and achieve easy raw materials and reaction conditions Mild, highly stereoselective effect
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Embodiment 1
[0066] Embodiment 1, the preparation of compound shown in formula I-a
[0067] The compound represented by formula I-a is prepared according to the following synthetic route:
[0068]
[0069] The above compound triethylamine (0.6072 g, 6 mmol) and amino alcohol (0.8531 g, 4 mmol) were weighed and dissolved in dichloromethane (4.0 mL), and acid chloride (0.4823 g, 4 mmol) in dichloromethane was added dropwise under ice bath. (4.0mL) solution, put it in an oil bath at room temperature and stirred for 18h. Water (50.0 mL) was added, extracted with ethyl acetate (3×50 mL), the organic layers were combined, washed with brine: 1M aqueous hydrochloric acid=1:1 (3×50 mL), washed with brine (3×50 mL), anhydrous sodium sulfate Dry, spin dry to give the amide as a white solid. Weigh the above amide compound (0.4461 g, 1.5 mmol) and ammonium molybdate (NH 4 ) 6 Mo 7 O 24 ·4H 2 O (0.4634 g, 0.375 mmol) was placed in a two-necked round-bottomed flask, a water separator and a refl...
Embodiment 3
[0078] Embodiment 3, the preparation of compound shown in formula I-c
[0079] The compound represented by formula I-c is prepared according to the following synthetic route:
[0080]
[0081] The above compound triethylamine (0.6072 g, 6 mmol) and amino alcohol (0.8531 g, 4 mmol) were weighed and dissolved in dichloromethane (4.0 mL), and acid chloride (0.6568 g, 4 mmol) in dichloromethane was added dropwise under ice bath. (4.0mL) solution, put it in an oil bath at room temperature and stirred for 18h. Water (50.0 mL) was added, extracted with ethyl acetate (3×50 mL), the organic layers were combined, washed with brine: 1M aqueous hydrochloric acid=1:1 (3×50 mL), washed with brine (3×50 mL), anhydrous sodium sulfate Dry, spin dry to give the amide as a white solid. Weigh the above amide compound (0.5752 g, 1.5 mmol) and ammonium molybdate (NH 4 ) 6 Mo 7 O 24 ·4H 2 O (0.4634 g, 0.375 mmol) was placed in a two-necked round-bottomed flask, a water separator and a refl...
Embodiment 4
[0084] Embodiment 4, the preparation of compound shown in formula I-d
[0085] The compound represented by formula I-d is prepared according to the following synthetic route:
[0086]
[0087] The above compound triethylamine (0.3034 g, 3 mmol) and amino alcohol (0.3024 g, 2 mmol) were weighed and dissolved in dichloromethane (4.0 mL), and acid chloride (0.2412 g, 2 mmol) in dichloromethane was added dropwise under ice bath. (4.0mL) solution, put it in an oil bath at room temperature and stirred for 18h. Water (50.0 mL) was added, extracted with ethyl acetate (3×50 mL), the organic layers were combined, washed with brine: 1M aqueous hydrochloric acid=1:1 (3×50 mL), washed with brine (3×50 mL), anhydrous sodium sulfate Dry, spin dry to give the amide as a white solid. Weigh the above amide compound (0.3530 g, 1.5 mmol) and ammonium molybdate (NH 4 ) 6 Mo 7 O 24 ·4H 2 O (0.4634 g, 0.375 mmol) was placed in a two-necked round-bottomed flask, a water separator and a refl...
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