Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/93147
Title: Asymmetric syntheses, structures and co-ordination chemistry of palladium(II) complexes containing a chiral P,S hybrid bidentate ligand
Authors: Leung, P.-H. 
Loh, S.-K.
Mok, K.F. 
White, A.J.P.
Williams, D.J.
Issue Date: 7-Dec-1996
Citation: Leung, P.-H.,Loh, S.-K.,Mok, K.F.,White, A.J.P.,Williams, D.J. (1996-12-07). Asymmetric syntheses, structures and co-ordination chemistry of palladium(II) complexes containing a chiral P,S hybrid bidentate ligand. Journal of the Chemical Society - Dalton Transactions (23) : 4443-4448. ScholarBank@NUS Repository.
Abstract: The chiral palladium complex (+) 589-di-μ-chloro-bis{(S)-1-[1-(dimethylamino)ethyl]-2-naphthyl- C2,N}dipalladium(II) has been used successfully to promote the asymmetric [4 + 2] Diels-Alder reaction between 3,4-dimethyl-1-phenylphosphole and phenyl vinyl sulfide. The cycloaddition product (-)-(1α,4α,5α,7R)-2,3-dimethyl-7-phenyl-5-(phenylsulfanyl)-7- phosphabicyclo[2.2.1]hept-2-ene was formed stereoselectively on the chiral palladium template and behaves as a bidentate ligand via its phosphorus and sulfur donor atoms. The chiral naphthylamine auxiliary and the new P,S bidentate ligand can be selectively released with retention of chirality by treatment with hydrochloric acid or 1,2-bis(diphenylphosphino)ethane respectively. The optical purity of the liberated heterobidentate compound has been confirmed by NMR spectroscopic studies. The absolute stereochemistries and the co-ordination properties of the enantiomerically pure P,S compound and its oxidized derivative have been established by single-crystal X-ray analyses.
Source Title: Journal of the Chemical Society - Dalton Transactions
URI: http://scholarbank.nus.edu.sg/handle/10635/93147
ISSN: 03009246
Appears in Collections:Staff Publications

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