Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with N-gulosyl nitrones
| Autor: | Kodai Takeda, Nobuyoshi Morita, Naka Mita, Masanori Sakamoto, Iwao Okamoto, Osamu Tamura, Hiroyuki Ishibashi |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_classification
Dysiherbaine Molecular Structure Organic Chemistry Stereoisomerism Biochemistry Nitrone Catalysis chemistry.chemical_compound Trimethylsilyl trifluoromethanesulfonate chemistry Organic chemistry Stereoselectivity Nitrogen Oxides Physical and Theoretical Chemistry Selectivity Furans Mannich reaction 2-trimethylsilyloxyfuran Hexoses |
| Zdroj: | Organicbiomolecular chemistry. 9(21) |
| ISSN: | 1477-0539 |
| Popis: | Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with L-gulose-derived chiral nitrones in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. The selectivity was strongly influenced by the bulkiness of the C-substituent of the nitrone: for example, C-benzyloxymethyl nitrone afforded four stereoisomers, whereas bulky C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]nitrone gave a single stereoisomer. The latter product was elaborated to afford key synthetic intermediates for polyoxin C and dysiherbaine. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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