960128-64-7Relevant academic research and scientific papers
COPPER CATALYZED HALOGENATON AND REACTION PRODUCTS
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, (2015/01/06)
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring a halogen from an sp2 to a benzylic carbon with good enantioselectivity and concomitant borylation of the Ar-halo bond. The resulting enantio-enriched benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom or carbon-carbon bond while maintaining high ee. The reaction can be used to efficiently prepare novel compounds and intermediates for the preparation of therapeutics and ligands for catalysis.
Chiral 1,2,3,4-tetrahydro-1-naphthylamine-derived phosphine-phosphoramidite ligand (THNAPhos): Application in highly enantioselective hydrogenations of functionalized C=C bonds
Qiu, Min,Hu, Xiang-Ping,Wang, Dao-Yong,Deng, Jun,Huang, Jia-Di,Yu, Sai-Bo,Duan, Zheng-Chao,Zheng, Zhuo
experimental part, p. 1413 - 1418 (2009/06/18)
We have recently reported a new chiral 1,2,3,4-tetrahydro-1-naphthylamine- derived phosphine-phosphoramidite ligand, (Rc,Ra)- THNAPhos, that is highly efficient in the rhodium-catalyzed asymmetrichydrog enation of a broad range of aenol ester phosphonates. To further demonstrate the utility of THNAPhos in asymmetric hydrogenation, in this paper, we describe its new application in the asymmetrichy drogenation of α-dehydroamino acid esters, enamides, dimethyl itaconate and α-enamido phosphonates. The results disclosed that the Rh/(Rc,Ra)-THNAPhos complex is highly effective for the enantioselective hydrogenation of these kinds of functionalized C=C olefins, affording the corresponding hydrogenation product in excellent enantioselectivities (normally over 99% ee).
Modular phosphine-aminophosphine ligands based on chiral 1,2,3,4-tetrahydro-1-naphthylamine backbone: A new class of practical ligands for enantioselective hydrogenations
Qiu, Min,Hu, Xiang-Ping,Huang, Jia-Di,Wang, Dao-Yong,Deng, Jun,Yu, Sai-Bo,Duan, Zheng-Chao,Zheng, Zhuo
experimental part, p. 2683 - 2689 (2009/10/14)
A series of new chiral phosphine-aminophosphine ligands [(R)-HW-Phos] has been prepared from (R)-1,2,3,4-tetrahydro-1-naphthylamine through a two-step procedure, and successfully applied in the rhodium-catalyzed asymmetric hydrogenation of various functionalized olefins such as α-enol ester phosphonates, α-enamido phosphonates, (Z)-β-(acylamino)acrylates and so on. Excellent enantioselectivities have been achieved in the hydrogenation of most substrates tested, demonstrating the high potential of these newly developed phosphine-aminophosphine ligands in asymmetric catalysis. The present research also discloses that these newly developed phosphine-aminophosphine ligands are more efficient than that derived from (S)-1-phenylethylamine, suggesting that the increased rigidity conferred by a cyclohexyl fragment in these phosphine-aminophosphine ligands has a positive effect in the asymmetric induction.
Highly enantioselective synthesis of α-hydroxy phosphonic acid derivatives by Rh-catalyzed asymmetric hydrogenation with phosphine- phosphoramidite ligands
Wang, Dao-Yong,Hu, Xiang-Ping,Huang, Jia-Di,Deng, Jun,Yu, Sai-Bo,Duan, Zheng-Chao,Xu, Xue-Feng,Zheng, Zhuo
, p. 7810 - 7813 (2008/09/19)
(Chemical Equation Presented) A class act: Unsymmetrical hybrid phosphine-phosphoramidite ligands with central and axial chirality are applied to the highly enantioselective hydrogenation of various enol ester phosphonates (see scheme; cod = cycloocta-1,5-diene). Enantioselectivities up to 99.9% ee are obtained for all classes of β-aryl, β-alkoxy, and β-alkyl substrates.
