化学
氢胺化
对映选择合成
烯丙基重排
催化作用
组合化学
亚胺
胺化
配体(生物化学)
芳基
手性配体
共轭体系
有机化学
生物化学
受体
聚合物
烷基
作者
Nathan J. Adamson,Haleh Jeddi,Steven J. Malcolmson
摘要
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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