BINOL-derived diphosphoramidites bearing unsymmetrical 1,2-diamine link and their application in asymmetric catalysis |
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| Authors: | Konstantin N. Gavrilov Alexei A. Shiryaev Ilya V. Chuchelkin Sergey V. Zheglov Eugenie A. Rastorguev Vadim A. Davankov Armin Börner |
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| Affiliation: | 1. Department of Chemistry, Ryazan State University, 46 Svoboda Street, 390000 Ryazan, Russian Federation;2. Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation;3. Leibniz-Institut für Katalyse an der Universität Rostock e.V., A.-Einstein-Str. 29a, 18059 Rostock, Germany |
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| Abstract: | New P,P-bidentate diastereomeric diphosphoramidite chiral ligands with mixed stereogenic elements and a C1 backbone symmetry have been prepared from (Sa)- and (Ra)-1,1′-binaphthyl-2,2′-diol (BINOL) and (S)-N-benzyl-1-(pyrrolidin-2-yl)methanamine and are fully characterized. The use of these ligands provides up to 84% ee in the Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate and up to 95% ee in the Rh-catalyzed asymmetric hydrogenation of α-dehydrocarboxylic acid esters. The results indicate that the catalytic performance is highly affected by the axial chirality of the binaphthyl moieties of the ligand and the nature of the solvent. |
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