Shanghai Jiao Tong University

Nippon Chemical Industrial Co., Ltd.

Delong Liu

Wanbin Zhang

Fang Quan Xie

Hui Guo

Li Luo

Yangang Liu

Genghong Hua

Jian Shang

The invention relates to an asymmetric hydrogenation method for ketone compounds, comprising the step of: under hydrogen atmosphere, in the presence of an in situ catalyst derived from a chiral ligand and a ruthenium salt, adding a ketone compound and a base into a second solvent to carry out an asymmetric hydrogenation for the ketone compound. The invention can obtain a conversion of 100% and a highest asymmetric inducement effect of 99.7% for the ketone compound. The invention has the advantages including simple procedure, high conversion and selectivity, good atom economy and good prospect of industrial application.

Asymmetric hydrogenation method for ketone compound

The invention affords C-symmetrical ruthenocene diphosphine ligands with surface chirality and their manufacture. The present invention uses (S)-(S)-1,1'-2(diphenylphosphino)-2,2&#x2032;-2[(S)-4-isopropyloxazolinyl] ruthenocene as raw material and the product is prepared through two or three steps of reaction. At the action of trifluoroacetic acid, (S)-(S)-1,1&#x2032;-2(diphenylphosphino)-2,2&#x2032;-2[(S)-4-isopropyloxazolinyl] ruthenocene first removes oxazoline and gets ester amides compound which then carries out ester exchange or reduction alkylation and gets the product of ruthenocene diphosphine ligand with surface chirality. The ligands prepared with the structure as follows from the invention can be used in all kinds of metallic catalysis asymmetric reaction and has good reaction activity and stereoselectivity, wherein R is methyl or ethyl, Ris linear or branched alkyl, cycloalkyl, alkoxy, aryl, aralkyl and alkyl amino. 

C2-symmetrical ruthenocene diphosphine ligands only with surface chirality and their manufacture

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Shanghai, China

Delong Liu