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|Title:||A rational approach to the design and synthesis of chiral organopalladium-amine complexes|
|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|
|Appears in Collections:||Staff Publications|
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