Chiral amido- and diamidophosphites with a peripheral pyridine ring in Pd-catalyzed asymmetric allylation
| Autor: | Sergey V. Zheglov, V. K. Gavrilov, Ilya A. Zamilatskov, Igor S. Mikhel, I. M. Novikov, Konstantin N. Gavrilov |
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| Rok vydání: | 2016 |
| Předmět: |
Allylic rearrangement
010405 organic chemistry Ligand Stereochemistry Enantioselective synthesis General Chemistry Alkylation 010402 general chemistry 01 natural sciences Medicinal chemistry Dimethyl malonate Pyrrolidine 0104 chemical sciences chemistry.chemical_compound chemistry Pyridine Amination |
| Zdroj: | Russian Chemical Bulletin. 65:2278-2285 |
| ISSN: | 1573-9171 1066-5285 |
| DOI: | 10.1007/s11172-016-1578-6 |
| Popis: | New chiral amidophosphite and diamidophosphite ligands with exocyclic pyridyl-containing substituents were obtained. Their efficiency in the Pd-catalyzed enantioselective allylic substitution was compared: in the sulfonylation of (E)-1,3-diphenylallyl acetate with sodium p-toluenesulfinate, the ee can reach 77%; its alkylation with dimethyl malonate and amination with pyrrolidine gave up to 80% and 74% ee, respectively. The asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexanecarboxylate can provide to 68% ee. The complexation of zinc(ii) 5,10,15,20-tetraphenylporphyrinate with diamidophosphite ligand and its influence on conversion and enantioselectivity of the process were studied. |
| Databáze: | OpenAIRE |
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