Expanding the substrate scope for C-H amination reactions: Oxidative cyclization of urea and guanidine derivatives

被引：158

作者：

Kim, M ^{[1
]}

Mulcahy, JV ^{[1
]}

Espino, CG ^{[1
]}

Du Bois, J ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 06期

关键词：

D O I：

10.1021/ol052920y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative C-H amination of N-trichloroethoxysulfonyl-protected ureas and guanidines is demonstrated to proceed in high yield for tertiary and benzylic-derived substrates. The success of these reactions is predicated on the choice of the electron-withdrawn 2,2,2-trichloroethoxysulfonyl (Tces) protecting group, the commercial catalyst Rh-2(esp)(2) (1-2 mol %), and toluene as solvent. The frequency with which the heterocyclic imidazolidin-2-ones and 2-aminoimidazolines appear as structural elements in both natural products and therapeutically designed molecules confers these methods with a large number of potential applications.

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页码：1073 / 1076

页数：4

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