Stereospecific internal alkylation of terminal gamma,delta-epoxy acrylates
Stereospecific internal alkylation of terminal gamma,delta-epoxy acrylates
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DOI：
10.1016/s0040-4039(97)00635-7
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发表时间：
1997-05-12
影响因子：
1.8
通讯作者：
Miyashita, M
中科院分区：
文献类型：
--
作者：
Miyazawa, M;Ishibashi, N;Miyashita, M
由D-甘露醇制备的手性末端γ，δ-环氧丙烯酸酯（S）-和（R）-4，5-环氧-2-戊烯酸乙酯（11）和（12）在水存在下通过三烷基铝的烷基化反应区域选择性地发生在γ位，即，在内部位置上，分别形成一个外形完全相反的单一产品。该方法为天然产物的合成提供了有用的手性配体。(C)1997 Elsevier Science Ltd.
The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal gamma,delta-epoxy acrylates prepared from D-mannitol, by trialkylaluminum in the presence of water occurs regioselectively at the gamma position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The method provides useful chiral synthons for natural product synthesis. (C) 1997 Elsevier Science Ltd.