期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 31, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202205159
关键词
Amination; Atroposelectivity; C-N Axis; Conjugation; Heterocycles
资金
- National Key R&D Program of China [2018YFA0903500]
- National Science Foundation of China [21602067]
- Hubei Technological Innovation Project [2019ACA125]
Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N-sulfonyl-3-arylaminoindoles with excellent optical purity. This method is valuable in enlarging the toolbox for atropochiral amine derivatives.
Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N-sulfonyl-3-arylaminoindoles with excellent optical purity. This reaction was furnished by 1,6-nucleophilic addition to p-quinone diimines. Control experiments suggest an ionic mechanism that differs from the radical addition pathway commonly proposed for 1,6-addition to quinones. The origin of 1,6-addition selectivity was investigated through computational studies. Preliminary studies show that the obtained 3-aminoindoles atropisomers exhibit anticancer activities. This method is valuable with respect to enlarging the toolbox for atropochiral amine derivatives.
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