Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with N-gulosyl nitrones |
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Authors: | Tamura Osamu Takeda Kodai Mita Naka Sakamoto Masanori Okamoto Iwao Morita Nobuyoshi Ishibashi Hiroyuki |
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Affiliation: | Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan. tamura@ac.shoyaku.ac.jp |
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Abstract: | 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. |
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