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

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33 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)632-635
Number of pages4
JournalOrganic Letters
Volume16
Issue number2
DOIs
Publication statusPublished - 2014 Mar 17

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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