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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

Active Publication Date: 2021-02-09
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is that the raw materials in the preparation method of isoindolinone compounds in the prior art are not easy to obtain, and the reaction efficiency or enantioselectivity are relatively low, and then provide a rhodium complex, its preparation Methods, Intermediates and Applications

Method used

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  • Rhodium complex, its preparation method, intermediate and application
  • Rhodium complex, its preparation method, intermediate and application
  • Rhodium complex, its preparation method, intermediate and application

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention discloses a rhodium complex, its preparation method, intermediate and application. The structure of the rhodium complex of the present invention is shown in formula (R)-K or (S)-K. The rhodium complex of the present invention exhibits better enantioselectivity and yield in the chiral synthesis of isoindolinone compounds.

Description

technical field [0001] The invention relates to a rhodium complex, its preparation method, intermediate and application. Background technique [0002] The C-H bond functionalization reaction catalyzed by the pentamethylcyclopentadiene rhodium complex can efficiently construct carbon-carbon bonds and carbon-heterobonds, and has been widely used in chemical synthesis. However, in the direct C–H functionalization reaction catalyzed by the pentamethylcyclopentadienyl rhodium complex, many reaction selectivity problems are often encountered and need to be solved. In order to adjust the selectivity of the reaction, a common strategy is to adjust the electronic and steric hindrance of the cyclopentadiene ligand of the rhodium complex. Some examples of chemoselectivity, regioselectivity, and diastereoselectivity of reactions controlled by cyclopentadienyl ligand modulation have been reported by the Rovis group and the Chang group [(a) T.K. Hyster, D.M. Dalton, T. Rovis. Chem.Sci.2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00B01J31/22C07D209/46C07F7/08C07C35/52C07C29/62C07C35/44C07C29/32C07C13/62C07C1/22
CPCB01J31/2295B01J2531/0225B01J2531/822B01J2540/20C07B2200/07C07C1/22C07C29/32C07C29/62C07D209/46C07F15/0073C07C2603/54C07C35/52C07C35/44C07C13/62
Inventor 游书力崔文俊
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI