期刊
CHEMICAL SCIENCE
卷 12, 期 5, 页码 1834-1842出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc05224h
关键词
-
资金
- NIH [GM110525]
Intermolecular asymmetric haloamination reactions are challenging due to high HalA of nitrogen atom, but using acetonitrile as nucleophile in catalytic asymmetric Ritter-type chloroamidation has led to successful synthesis of 1,2-chloroamide products with enantiomeric excess greater than 95%.
Intermolecular asymmetric haloamination reactions are challenging due to the inherently high halenium affinity (HalA) of the nitrogen atom, which often leads to N-halogenated products as a kinetic trap. To circumvent this issue, acetonitrile, possessing a low HalA, was used as the nucleophile in the catalytic asymmetric Ritter-type chloroamidation of allyl-amides. This method is compatible with Z and E alkenes with both alkyl and aromatic substitution. Mild acidic workup reveals the 1,2-chloroamide products with enantiomeric excess greater than 95% for many examples. We also report the successful use of the sulfonamide chlorenium reagent dichloramine-T in this chlorenium-initiated catalytic asymmetric Ritter-type reaction. Facile modifications lead to chiral imidazoline, guanidine, and orthogonally protected 1,2,3 chiral tri-amines.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据