Catalytic enantioselective fluorination of oxindoles
Catalytic enantioselective fluorination of oxindoles
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DOI：
10.1021/ja0513077
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发表时间：
2005-07-27
影响因子：
15
通讯作者：
Sodeoka, M
中科院分区：
文献类型：
--
作者：
Hamashima, Y;Suzuki, T;Sodeoka, M
我们开发了一种高效的催化氧化吲哚衍生物的对映选择性手性拆分方法。在催化量的手性Pd络合物2（2.5摩尔%）的存在下，各种底物，包括芳基和烷基取代的羟吲哚，氟化在一个高度对映选择性的方式（高达96%ee）。此外，当R是一个氢原子，不对称选择性的取代，然后溶剂分解得到一个单氟化酯与高达93%ee。据我们所知，这是第一个例子的催化不对称选择性取代羟吲哚。
We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex2(2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluorinated in a highly enantioselective manner (up to 96% ee). In addition, when R was a hydrogen atom, enantioselective fluorination followed by solvolysis gave a monofluorinated ester with up to 93% ee. To our knowledge, this is the first example of catalytic enantioselective fluorination of oxindoles.