The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketimines
Jazyk angličtina Země Anglie, Velká Británie Médium print
Typ dokumentu časopisecké články
PubMed
29083001
DOI
10.1039/c7ob02408h
Knihovny.cz E-zdroje
- MeSH
- benzensulfonáty chemie MeSH
- iminy chemie MeSH
- isatin chemie MeSH
- methan chemie MeSH
- nitrily chemie MeSH
- stereoizomerie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- 1-fluoro-1-nitro(phenylsulfonyl)methane MeSH Prohlížeč
- benzensulfonáty MeSH
- iminy MeSH
- isatin MeSH
- ketimine MeSH Prohlížeč
- methan MeSH
- nitrily MeSH
An asymmetric organocatalytic addition of fluorinated phenylsulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine. This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7 : 1 dr) and excellent enantioselectivity (up to 98/96% ee).
Department of Inorganic Chemistry Charles University Hlavova 8 12843 Prague Czech Republic
Department of Organic Chemistry Charles University Hlavova 8 12843 Prague Czech Republic
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