期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 21, 页码 8574-8583出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b02637
关键词
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资金
- National Science Foundation [CHE-1800012]
- Duke University
- NIGMS [T32GM007105]
- Duke Chemistry Department
In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.
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