1,1'-biphenyls axial chirality diphosphinidene amide ligand connected at 5,5' position
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A bisphosphonite, axial chirality technology, used in the chemical industry to achieve the effect of high reactivity
Inactive Publication Date: 2008-04-30
SHANGHAI JIAO TONG UNIV
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However, the research on the reactivity and enantioselectivity of asymmetric catalytic reactions by dihedral angle size of bisphosphonamidite ligands containing axial chirality has not been reported.
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[0025] The embodiments of the present invention are described in detail below: the present embodiment is implemented under the premise of the technical solution of the present invention, and detailed implementation and specific operation process are provided, but the protection scope of the present invention is not limited to the following implementation example.
[0026] (1) Preparation of compound V from 3-bromo-4-nitroanisole
[0027] Compound VI (3.2 g, 13.9 mmol) and activated copper powder (3.6 g, 55.6 mmol) were heated to 170° C. for four hours. Washed with benzene and ethyl acetate, the solvent was evaporated, and the residue was recrystallized with acetonitrile to obtain product V (1.7 g, 80%).
[0029] (2) Preparation of compound VI from compound V
[0030] Compound V (1.2g, 4.1mmol) and anhydrous lithium chloride (1.0g, 24.5mmol) were heated under re...
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Abstract
The invention relates to 1, 1(1)-diphenyl axial chiral bis di-phosphinous amide ligand connected at 5,5(1) position in the chemical technical field. The structural formula of the invention is shown as follows: in the formula, n is equal to 5, 6, 7, 8, 9, 10, 11, or 12; R1 is equal to hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, the alkyl of 1-8 carbon, or the alkoxyl of the 1-8 carbon; R2 is equal to the hydrogen, the fluorine, the chlorine, the bromine, the iodine, the trifluoromethyl, the alkyl of the 1-8 carbon, or the alkoxyl of the 1-8 carbon; R3 is equal to the hydrogen, the fluorine, the chlorine, the bromine, the iodine, the trifluoromethyl, the alkyl of the 1-8 carbon, or the alkoxyl of the 1-8 carbon; R4 is equal to the hydrogen, the fluorine, the chlorine, the bromine, the iodine, the trifluoromethyl, the alkyl of the 1-8 carbon, or the alkoxyl of the 1-8 carbon; R5 is equal to the hydrogen, the fluorine, the chlorine, the bromine, the iodine, the trifluoromethyl, the alkyl of the 1-8 carbon, or the alkoxyl of the 1-8 carbon; the ligand can be appliable to various unsymmetrical reactions catalyzed by metal, and have very high reaction activity and stereoselectivity.
Description
technical field [0001] The invention relates to a compound in the technical field of chemical industry, in particular to a 1,1'-biphenyl-type axial chiral bisphosphonite amide ligand connected at the 5,5' position. Background technique [0002] The key to asymmetric catalytic synthesis is how to design and synthesize chiral catalysts with high selectivity and catalytic activity, in which chiral ligands are the source of asymmetric induction and control of catalysts. C 2 Type chiral bisphosphine ligands, due to their special structure, are widely used in metal-catalyzed asymmetric hydrogenation reactions, such as asymmetric catalytic hydrogenation of alkenes, allyl alkylation reactions and so on. After 30 years of development, a large number of bisphosphine ligands have emerged. After years of research, the axial chiral bisphosphine ligand BINAP containing the binaphthyl structure has been successfully applied to the industrial production of optically active compounds. Sin...
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