Diamidophosphites with remote P1-stereocentres and their performance in Pd-catalyzed enantioselective reactions |
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| Institution: | 1. Department of Chemistry, Ryazan State University, 46 Svoboda Street, 390000 Ryazan, Russian Federation;2. A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskiy prospekt 31, 119071 Moscow, Russian Federation;1. College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, People’s Republic of China;2. College of Science, Nanjing Forestry University, Nanjing 210037, People’s Republic of China;3. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore;1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary;2. Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, 1521 Budapest, Hungary;1. Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02 097 Warsaw, Poland;2. Department of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60 780 Poznań, Poland;3. Department of Histology and Embryology, First Faculty of Medicine, Medical University of Warsaw, Chałubiński 5, 02 004 Warsaw, Poland;1. Department of Radiology, Ochsner Clinic Foundation, and The University of Queensland School of Medicine, Ochsner Clinical School, New Orleans, Louisiana;2. Commission on Human Resources, American College of Radiology, Reston, Virginia;3. Sage Computing, Inc, Reston, Virginia |
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| Abstract: | Diamidophosphite ligands based on 1,1′-bis(hydroxymethyl)ferrocene or N1,N2-bis((S)-1-hydroxy-3,3-dimethylbutan-2-yl)oxalamide and bearing 1,3,2-diazaphospholidine rings with stereogenic phosphorus atoms were obtained. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate, up to 70% ee in Pd-catalyzed desymmetrizations of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol bis-carbamate and up to 80% ee in Pd-catalyzed allylic alkylations of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate. Results obtained with a diamidophosphite containing an oxalamide framework show the considerable potential of such ligands in enantioselective catalysis. |
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