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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.
Fulltext Permission: restricted
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Student Reports (FYP/IA/PA/PI)

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