Please use this identifier to cite or link to this item:
|Title:||Asymmetric synthesis of cyano- functionalised-1, 3-diphosphine via organopalladium promoted hydrophosphination reaction.||Authors:||Lee, Zhi Yi.||Keywords:||DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis||Issue Date:||2010||Abstract:||The asymmetric hydrophosphination reaction involving (Triphenylphosphoranylidene)acetonitrile and diphenylphosphine was carried out by utilizing palladium complex containing ortho-metalated (R)-(dimethylamino)ethyl)naphthalene as the chiral auxiliary. The cyano-functionalized monophosphine substrate were synthesized from 3- chloro-1,1-diethoxypropane via a versatile one-pot process. Subsequent hydrophosphination of coordinated cyano-functionalized phosphine substrates promoted by the chiral auxillary gave corresponding functionalized 1, 3-diphosphine product. Functional group transformation of the cyano group to formyl group was performed by selective reduction of diphosphine palladium complex by using DIBAL-H. The reaction proceeded regiospecifically and stereospecifically to give the corresponding formyl-functionalised 1, 3-diphosphine products. The coordination properties and absolute configurations of the novel formyl-functionalized 1, 3-diphosphine complexes were established by single crystal X-ray crystallography. The enantiomerically pure formyl functionalized diphosphine ligand could be subsequently liberated stereospecifically by treatment of the corresponding dichloro palladium complexes with aqueous potassium cyanide in high yield.||URI:||http://hdl.handle.net/10356/40654||Fulltext Permission:||restricted||Fulltext Availability:||With Fulltext|
|Appears in Collections:||SPMS Student Reports (FYP/IA/PA/PI)|
Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.