Please use this identifier to cite or link to this item: https://doi.org/10.1021/ic030018l
Title: A rational approach to the design and synthesis of chiral organopalladium-amine complexes
Authors: Li, Y.
Selvaratnam, S.
Vittal, J.J. 
Leung, P.-H. 
Issue Date: 19-May-2003
Citation: Li, Y., Selvaratnam, S., Vittal, J.J., Leung, P.-H. (2003-05-19). A rational approach to the design and synthesis of chiral organopalladium-amine complexes. Inorganic Chemistry 42 (10) : 3229-3236. ScholarBank@NUS Repository. https://doi.org/10.1021/ic030018l
Abstract: A new chiral auxiliary, (±)-N,N-dimethyl-1-(2,5-dimethylphenyl)ethylamine, was designed and synthesized in two steps from 1-acetyl-2,5-dimethylbenzene. Its cyclopalladated dimeric complex could be efficiently resolved via the formation of (S)-prolinate derivatives. Both hand forms of the complex could be obtained in similar yields. Despite the enormous inter-chelate steric constraints, the bulky monodentate ligand 3,4-dimethyl-1-phenylphosphole (DMPP) is able to coordinate regiospecifically to the orthopalladated 2,5-dimethylbenzylamine unit trans to the NMe2 group. Compared to its naphthylamine analogue, the orthopalladated 2,5-dimethylbenzylamine complex exhibits a significantly higher stereoselectivity in the chiral template promoted asymmetric cycloaddition reaction between DMPP and ethyl vinyl ketone.
Source Title: Inorganic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/92995
ISSN: 00201669
DOI: 10.1021/ic030018l
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