Synthesis method of chiral monophosphorus ligand

Abstract

The invention discloses a synthesis method of chiral mono-phosphorus ligand 2-diphenylphosphine-2'-methoxy-1,1'-binaphthyl. The chiral mono-phosphorus ligand is widely applied to the asymmetric catalysis field. The synthesis method comprises the following steps: allowing optically pure binaphthalene monomethyl ether to react with trifluoromethanesulfonic anhydride to obtain 2-trifluoromethyl sulfonyloxy-2'-methoxy-1,1'-binaphthyl; and allowing the obtained compound to react with diphenylphosphine oxide under the catalytic action of palladium to obtain 2-diphenylphosphine acyl-2'-methoxy-1,1'-binaphthyl, and then reducing with trichlorosilane to finally obtain the optically pure mono-phosphorus ligand 2-diphenylphosphine-2'-methoxy-1,1'-binaphthyl. The synthesis method has short synthetic route and high atom economy, thus greatly lowering cost; and the synthetic route is shown in the following reaction equation.

Description

technical field The invention belongs to organic chemistry, asymmetric catalysis, and synthesis of chiral ligands. More specifically, it uses binaphthyl diol monomethyl ether to synthesize 2-diphenylphosphine-2'-methoxyl-1,1'- binaphthyl. Background technique (S)- or (R)-2-diphenylphosphine-2'-methoxy-1,1'-binaphthyl is an important chiral ligand, which can be used in palladium, rhodium, nickel and other metal catalysis Asymmetric allylation, hydrosilation of alkenes, hydroboration of 1,3-enynes and other asymmetric reactions (T.Hayashi.Acc.Chem.Res.2000, 33:354-362). It is reported in the literature that the method for synthesizing 2-diphenylphosphine-2'-methoxy-1,1'-binaphthyl is to generate binaphthyl diol bistrifluoromethane from binaphthyl diol and two moles of trifluoromethanesulfonic anhydride Sulfonate, then under palladium catalysis, diphenylphosphine oxide reacts with one of the trifluoromethanesulfonate groups, and the remaining trifluoromethanesulfonate group ...

AI Technical Summary

Problems solved by technology

The synthesis method in the literature does not conform to the principle of atom economy, and the route is longer, there are more three wastes, it does not meet the requirements of green chemistry, and the cost is much higher

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