Catalytic enantioselective fluorination of oxindoles

被引：314
作者：
Hamashima, Y
Suzuki, T
Takano, H
Shimura, Y
Sodeoka, M [1 ]
机构：
[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Miyagi 9808577, Japan
[2] JST, PRESTO, Wako, Saitama 3510198, Japan
[3] RIKEN, Wako, Saitama 3510198, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 29期
关键词：
D O I：
10.1021/ja0513077
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (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. Copyright © 2005 American Chemical Society.
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页码：10164 / 10165
页数：2
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