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
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.
