The enantioselective synthesis of ( R ) 2 trimethylsilyl 2 hydroxyl propionitrile by ( R ) oxynitrilase contained in defatted apple seed meal in a biphasic system was successfully performed. The influences o...The enantioselective synthesis of ( R ) 2 trimethylsilyl 2 hydroxyl propionitrile by ( R ) oxynitrilase contained in defatted apple seed meal in a biphasic system was successfully performed. The influences of some factors on the reaction were investigated systematically. Diisopropyl ether was found to be the best for this reaction among all the organic solvents examined. The optimal concentration of defatted apple seed meal, aqueous phase content, concentrations of acetyltrimethylsilane and acetone cyano^hydrin, buffer pH, reaction temperature were 4% ( W/V ), 23% ( V/V ), 20 mmol·L -1 , 40 mmol·L -1 , pH=5 0 and 40 ℃, respectively, under which the initial reaction rate, substrate conversion and product enantiomeric excess were 9 4 mmol·L -1 ·h -1 , 99% and >99%, respectively.展开更多
The nitrile compounds are present in a variety of biologically active natural products and pharmaceuticals,and the nitrile groups are versatile synthetic intermediates to other functionalized compounds.Herein,the asym...The nitrile compounds are present in a variety of biologically active natural products and pharmaceuticals,and the nitrile groups are versatile synthetic intermediates to other functionalized compounds.Herein,the asymmetric reduction ofα,β-unsaturated nitriles with water as a hydrogen source is reported.The reaction is catalyzed by the complex of[Ir(COD)Cl]_(2)and(R_(a),S)-Ph-Bn-SiPhox,and allows the preparation of useful enantioenriched chiral 3,3-disubstituted propionitriles with high optical purities in mild conditions.展开更多
基金ProjectsupportedbytheNationalNaturalScienceFoundationofChina (No .20076019)andtheNaturalScienceFoundationofGuang dongProvince (No .0 0 0 44 4)
文摘The enantioselective synthesis of ( R ) 2 trimethylsilyl 2 hydroxyl propionitrile by ( R ) oxynitrilase contained in defatted apple seed meal in a biphasic system was successfully performed. The influences of some factors on the reaction were investigated systematically. Diisopropyl ether was found to be the best for this reaction among all the organic solvents examined. The optimal concentration of defatted apple seed meal, aqueous phase content, concentrations of acetyltrimethylsilane and acetone cyano^hydrin, buffer pH, reaction temperature were 4% ( W/V ), 23% ( V/V ), 20 mmol·L -1 , 40 mmol·L -1 , pH=5 0 and 40 ℃, respectively, under which the initial reaction rate, substrate conversion and product enantiomeric excess were 9 4 mmol·L -1 ·h -1 , 99% and >99%, respectively.
基金grateful to the National Natural Science Foundation of China(Nos.21961045 and 22061048)the Basic Research Project of Chongqing Academy of Chinese Materia Medica(No.jbky20190028)+2 种基金the Fund Project of Yunnan Key Laboratory of Pharmacology for Natural Products(No.YKLPNP-K2303)Yunnan Provincial Key Laboratory Construction Plan Funding of UniversitiesYunnan Provincial Engineering Research Center Construction Plan Funding of Universities for their financial support.
文摘The nitrile compounds are present in a variety of biologically active natural products and pharmaceuticals,and the nitrile groups are versatile synthetic intermediates to other functionalized compounds.Herein,the asymmetric reduction ofα,β-unsaturated nitriles with water as a hydrogen source is reported.The reaction is catalyzed by the complex of[Ir(COD)Cl]_(2)and(R_(a),S)-Ph-Bn-SiPhox,and allows the preparation of useful enantioenriched chiral 3,3-disubstituted propionitriles with high optical purities in mild conditions.
