Stereoselective Vinylogous Mannich Reaction of 2-Trimethylsilyloxyfuran on to N-Gulosyl Nitrones
Stereoselective Vinylogous Mannich Reaction of 2-Trimethylsilyloxyfuran on to N-Gulosyl Nitrones
复制标题
2-三甲基硅氧基呋喃与 N-古洛基硝酮的立体选择性乙烯基曼尼希反应
DOI：
10.1039/c1ob06067h
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发表时间：
2011
影响因子：
3.2
通讯作者：
Hiroyuki Ishibashi
中科院分区：
文献类型：
--
作者：
Osamu Tamura;Kodai Takeda;Naka Mita;Masanori Sakamoto;Iwao Okamoto;Nobuyoshi Morita;Hiroyuki Ishibashi
研究了2-三甲基硅氧基呋喃与L-古洛糖衍生的手性硝酮在催化量三氟甲磺酸三甲基硅酯存在下的立体选择性乙烯基Mannich反应。选择性受硝酮的C-取代基的体积的强烈影响：例如，C-苄氧基甲基硝酮得到四种立体异构体，而体积大的C-[（4S）-2，2-二甲基-1，3-二氧戊环-4-基]硝酮得到单一立体异构体。后一种产物被加工以提供多氧霉素C和dysiherbaine的关键合成中间体。
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.