Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/40654
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)

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