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Borane Catalyzed Redox Isomerization of 2-Amino Chalcones: Hydride Abstraction or Hydride Migration?
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2021-08-19 , DOI: 10.1002/ejoc.202100883 Rundong Zhou 1 , Jan Paradies 2
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2021-08-19 , DOI: 10.1002/ejoc.202100883 Rundong Zhou 1 , Jan Paradies 2
Affiliation
The borane catalyzed redox isomerization of 2-amino chalocones was developed. Mechanistic investigations by kinetic, isotopic labelling, and competition experiments as well as computational studies corroborate the concerted [1,5] hydride shift as operative mechanism. The redox isomerization products are obtained in high yield and up to >95 : 5 diastereoselectivity.
中文翻译:
硼烷催化 2-氨基查耳酮的氧化还原异构化:氢化物提取或氢化物迁移?
开发了硼烷催化的 2-氨基查耳酮的氧化还原异构化。通过动力学、同位素标记和竞争实验以及计算研究进行的机理研究证实了协同 [1,5] 氢化物转移是操作机制。氧化还原异构化产物以高产率和高达 >95:5 的非对映选择性获得。
更新日期:2021-08-19
中文翻译:
硼烷催化 2-氨基查耳酮的氧化还原异构化:氢化物提取或氢化物迁移?
开发了硼烷催化的 2-氨基查耳酮的氧化还原异构化。通过动力学、同位素标记和竞争实验以及计算研究进行的机理研究证实了协同 [1,5] 氢化物转移是操作机制。氧化还原异构化产物以高产率和高达 >95:5 的非对映选择性获得。