Chiral β-Iactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical comm...Chiral β-Iactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stereocontrolled construction of four-membered ring （mini-sized） β-lactams and cyclobutanones via an Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation, providing the corresponding optically active four-membered ring carbonyl products bearing an α-chiral carbon center with excellent yields （up to 99%） and enantioselectivities （up to 98%） under mild reaction conditions （1.0-2.5 bar H2 for 1.0-10 h）. The reaction presents wide substrate scope. Diverse transformations of the catalyzed products were also conducted to show the potential utility of this protocol.展开更多
Tropos phosphine-oxazoline ligands have shown interesting coordination behavior and excellent chiral inducing ability in asymmetry catalysis.Here we present a convenient and economic route for the synthesis of this ty...Tropos phosphine-oxazoline ligands have shown interesting coordination behavior and excellent chiral inducing ability in asymmetry catalysis.Here we present a convenient and economic route for the synthesis of this type of ligands.According to this new route,the ligands with different electronic and steric properties have been prepared successfully.展开更多
Herein,we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand.The transformation shows good functional group toler...Herein,we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand.The transformation shows good functional group tolerance,and gives the hydrogenated prod-ucts with excellent yields(up to 99%)and enantioselectivities(up to 98%ee).A gram-scale reaction was also carried out,and pro-vided the hydrogenated product in excellent yield with no erosion in enantioselectivity.Finally,the transformation of the hydrogen-ated product provided an efficient approach for the synthesis of the intermediate of a HIV protease inhibitor.展开更多
基金We thank the Shanghai Municipal Education Commission （No. 201701070002E00030）, the Science and Technology Commission of Shanghai Municipality （No. 15JC1402200）, and the National Natural Science Foundation of China （Nos. 21472123, 21572131, 21620102003） for financial support.
文摘Chiral β-Iactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stereocontrolled construction of four-membered ring （mini-sized） β-lactams and cyclobutanones via an Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation, providing the corresponding optically active four-membered ring carbonyl products bearing an α-chiral carbon center with excellent yields （up to 99%） and enantioselectivities （up to 98%） under mild reaction conditions （1.0-2.5 bar H2 for 1.0-10 h）. The reaction presents wide substrate scope. Diverse transformations of the catalyzed products were also conducted to show the potential utility of this protocol.
基金supported by the National Natural Science Foundation of China (20772081)Science and Technology Commission of Shanghai Municipality (09431902500)
文摘Tropos phosphine-oxazoline ligands have shown interesting coordination behavior and excellent chiral inducing ability in asymmetry catalysis.Here we present a convenient and economic route for the synthesis of this type of ligands.According to this new route,the ligands with different electronic and steric properties have been prepared successfully.
基金supported by the National KeyR&D Programof China(No.2018YFE0126800)National Natural Science Foundation of China(Nos.22001164,21620102003 and 21991112)+2 种基金Shanghai Municipal Education Commission(No.201701070002E00030)Shanghai Pujiang Program(20PJ1406400)the startup funding from Shanghai Jiao Tong University。
文摘Herein,we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand.The transformation shows good functional group tolerance,and gives the hydrogenated prod-ucts with excellent yields(up to 99%)and enantioselectivities(up to 98%ee).A gram-scale reaction was also carried out,and pro-vided the hydrogenated product in excellent yield with no erosion in enantioselectivity.Finally,the transformation of the hydrogen-ated product provided an efficient approach for the synthesis of the intermediate of a HIV protease inhibitor.
