Rhodium complex, its preparation method, intermediate and application
A compound and reaction technology, applied in the field of rhodium complexes, can solve the problems of difficult acquisition of raw materials, low reaction efficiency or enantioselectivity
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Embodiment 1
[0187] Example 1: Synthesis of multi-substituted cyclopentadiene and its rhodium complex based on 1,1'-binaphthalene skeleton:
[0188]
[0189] Synthesis of Compound (R)-V-1: Compound (R)-VI-1 (727mg, 1.53mmol, synthesized according to the method reported in Eur.J.Org.Chem.2015, 1887-1893) was dissolved in toluene (270mL) After heating and stirring at 120°C for 15 minutes, a toluene solution (50mL) of dicobalt octacarbonyl (1.05g, 3.06mmol) was added via a syringe pump (dropping rate 12mL / h). Cool to room temperature, filter through a short column of silica gel to remove black insoluble matter, wash with ethyl acetate, and concentrate the filtrate under reduced pressure. Purify by silica gel column chromatography (petroleum ether / dichloromethane 50 / 1) to obtain compound (R)-V-1.
[0190]
[0191] Orange foam, 500mg, yield 65%.[α]25D=+195.1(c=0.20, chloroform); IR (film)ν max =3050,2957,2897,2851,1681,1595,1540,1508,1428,1405,1362,1303,1242,1219,1174,1092,1021,893,840,...
Embodiment 2
[0208] Compound (S)-K4 was prepared using compound (S)-VI-1 as a raw material, and the synthesis method was the same as in Example 1.
[0209]
[0210] Red-black solid, 151 mg, yield 77%, m.p.>280°C. [α]30D=-219.9 (c=0.05, chloroform) HRMS (MALDI-FT) m / z: calculated value C 60 h 51 Cl 4 Rh + [M+H] + :1117.0849, the measured value is 1117.0850.
Embodiment 3
[0212]
[0213] Using corresponding raw materials, synthesized according to the synthesis method of Example 1, red-black solid, 145 mg, yield 78%, m.p.>280 ° C. HRMS (MALDI-FT) m / z: calculated value C 64 h 59 Cl 4 o 4 Rh 2 + [M+H] + :1237.1272, the measured value is 1237.1274.
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