Loading patent…
AssigneeZhejiang University
InventorsShengming Ma, Yuchen Zhang
Estimating the term…
The present invention relates to the design and synthesis of a class of novel chiral phosphine ligand, 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane, and use in asymmetric catalytic reactions, such as asymmetric catalytic synthesis of pyrazoline-5-one with a chiral quaternary carbon center, i.e., highly enantioselective synthesis of 3-methyl-4-benzyl-4-(2-butyl-2,3-butadienyl)pyrazoline-5-one by using 3-methyl-4-benzylpyrazoline-5-one and benzyl (2-butyl-2,3-butadienyl) carbonate with tris(dibenzylideneacetone)dipalladium-chloroform adduct and this novel ligand as catalysts. The ligand designed by this present invention has the following advantages: the structure is novel, the synthesis and enlarge are simple, the enantioselective control effect in the practical reaction is excellent, which has a broad application prospect in chiral catalysis.
1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane chiral phosphine ligands, wherein, the said 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane has the following structure as formula(I):
A method for preparing 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane, which comprises reacting, in an organic solvent, using-1,2-disubstituted-1,2-diaminoethane, diphenylphosphinoacetic acid, p-dimethylaminopyridine and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride as reaction raw materials to obtain 1,2-bis(diphenylphosphonylalkylamido)-1,2-disubstituted ethane through an amidation reaction, wherein said reaction has the following reaction equation:
A method for preparing 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane, which comprises reacting in an organic solvent, N-hydroxysuccinimide diphenylphosphonyl alkyl acid ester and 1,2-disubstituted-1,2-diaminoethane as reaction raw materials to obtain the said 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane through an amidation reaction, wherein said reaction has the following reaction equation:
Chiral 3-methyl-4-benzyl-4-(2-alkyl-2,3-butadienyl)pyrazoline-5-one compounds, wherein, the said chiral 3-methyl-4-benzyl-4-(2-alkyl-2,3-butadienyl)pyrazoline-5-one compounds have the following structure as formula(6):
Dependencies are inferred from the claim text.