Highly enantioselective Rh-Catalyzed Alkenylation of imines: Synthesis of Chiral Allylic Amines via Asymmetric addition of Potassium Alkenyltrifluoroborates to N-Tosyl imines

Balraj Gopula, Chien Wei Chiang, Way Zen Lee, Ting Shen Kuo, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

40 引文 斯高帕斯(Scopus)

摘要

For the first time, simple N-tosyl aryl aldimines, prepared from the condensation of tosyl amide and aromatic aldehydes, can be used as substrates in the rhodium catalyzed 1,2- addition reaction using alkenylboron nucleophiles. In the presence of 1.5 mol % of [RhCl(1e)]2, enantioselective addition of various potassium alkenyltrifluoroborates to aryl aldimines furnished the corresponding chiral allylic amines in 73-96% yield and 72->99.5% ee. Notably, this method efficiently provides the di-, tri-, and tetrasubstituted allylic N-tosyl amines with high asymmetric induction.

原文英語
頁(從 - 到)632-635
頁數4
期刊Organic Letters
16
發行號2
DOIs
出版狀態已發佈 - 2014 1月 17

ASJC Scopus subject areas

  • 生物化學
  • 物理與理論化學
  • 有機化學

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