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

Research output: Contribution to journalArticle

29 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

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Alkenylation
Imines
imines
Amines
potassium
Potassium
amines
Rhodium
Nucleophiles
Addition reactions
nucleophiles
synthesis
rhodium
aldehydes
Aldehydes
Amides
amides
Condensation
induction
condensation

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Highly enantioselective Rh-Catalyzed Alkenylation of imines : Synthesis of Chiral Allylic Amines via Asymmetric addition of Potassium Alkenyltrifluoroborates to N-Tosyl imines. / Gopula, Balraj; Chiang, Chien Wei; Lee, Way-Zen; Kuo, Ting Shen; Wu, Ping Yu; Henschke, Julian P.; Wu, Hsyueh-Liang.

In: Organic Letters, Vol. 16, No. 2, 17.03.2014, p. 632-635.

Research output: Contribution to journalArticle

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AU - Gopula, Balraj

AU - Chiang, Chien Wei

AU - Lee, Way-Zen

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AU - Wu, Ping Yu

AU - Henschke, Julian P.

AU - Wu, Hsyueh-Liang

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AB - 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.

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