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|Title:||Asymmetric synthesis of functionalized chiral diphosphines via organopalladium promoted hydrophosphination and diels-alder reactions||Authors:||Yuan, Mingjun||Keywords:||DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
|Issue Date:||2011||Source:||Yuan, M. J. (2011). Asymmetric synthesis of functionalized chiral diphosphines via organopalladium promoted hydrophosphination and diels-alder reactions. Doctoral thesis, Nanyang Technological University, Singapore.||Abstract:||This thesis describes the asymmetric synthesis of functionalized chiral diphosphines via enantiomeric organopalladium complex (R-26) promoted asymmetric hydrophosphination and Diels-Alder reactions. Introduction of functionalities on chiral diphosphines using organic transformations with palladium template as protection is also demonstrated. In Chapter 1, a brief introduction on the synthesis and application of chiral diphosphines, research development in our research group and the aims of this project is presented. In Chapter 2, the ester- and keto-functionalized allylic monophosphine palladium complexes containing the ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary were synthesized via a versatile one-pot process. Subsequent asymmetric hydrophosphination of the coordinated allylic phosphine substrates generated the functionalized chiral 1,2-bis(diphenylphosphino)ethane products. The coordination properties and absolute configurations of the diphosphine ligands were established by single crystal X-ray crystallography. The optically pure 1,2-bis(diphenylphosphino)ethane ligands with ester and keto functionalities could be liberated in high yields from the corresponding dichloro palladium complexes by treatment with aqueous potassium cyanide.||URI:||https://hdl.handle.net/10356/43675||DOI:||10.32657/10356/43675||Fulltext Permission:||open||Fulltext Availability:||With Fulltext|
|Appears in Collections:||SPMS Theses|
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