Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones
| Autor: | Alexander N. Reznikov, M. R. Baimuratov, Victor B. Rybakov, Anastasiya E. Sibiryakova, Eugene Golovin, Yuri N. Klimochkin |
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| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
education
Medicinal chemistry Full Research Paper Adduct Catalysis Stereocenter lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Michael addition nitroalkenes lcsh:Science Chemistry Organic Chemistry Diastereomer Enantioselective synthesis asymmetric catalysis chiral diamine ligands humanities Nitro Michael reaction Organic synthesis lcsh:Q ketosulfones nickel complexes |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 1289-1297 (2019) |
| ISSN: | 1860-5397 |
| Popis: | Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate. Conditions for the preparation of individual diastereomers were found. |
| Databáze: | OpenAIRE |
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