The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketimines
Language English Country England, Great Britain Media print
Document type Journal Article
PubMed
29083001
DOI
10.1039/c7ob02408h
Knihovny.cz E-resources
- MeSH
- Benzenesulfonates chemistry MeSH
- Imines chemistry MeSH
- Isatin chemistry MeSH
- Methane chemistry MeSH
- Nitriles chemistry MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 1-fluoro-1-nitro(phenylsulfonyl)methane MeSH Browser
- Benzenesulfonates MeSH
- Imines MeSH
- Isatin MeSH
- ketimine MeSH Browser
- Methane MeSH
- Nitriles 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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