A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes

Balraj Gopula, Hao Wei Zeng, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

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Abstract

A method providing expeditious access to chiral allylic amines via a Rh(I)/bicyclo[2.2.1]heptadiene-catalyzed enantioselective alkenylation of N-tosyl aldimines with potassium alkenyltrifluoroborates under microwave irradiation is described. The rate of the asymmetric 1,2-addition reaction, conducted in the presence of 1 mol % of the catalyst, was significantly enhanced as compared to when the standard heating method was applied while still providing the corresponding products without decrease in enantioselectivity.

LanguageEnglish
Pages312-316
Number of pages5
JournalJournal of the Chinese Chemical Society
Volume65
Issue number3
DOIs
Publication statusPublished - 2018 Mar 1

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Alkenylation
Rhodium
Addition reactions
Microwave irradiation
Enantioselectivity
Amines
Potassium
Microwaves
Heating
Catalysts

Keywords

  • Chiral allylic amine
  • Enantioselective
  • Microwave irradiation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes. / Gopula, Balraj; Zeng, Hao Wei; Wu, Ping Yu; Henschke, Julian P.; Wu, Hsyueh Liang.

In: Journal of the Chinese Chemical Society, Vol. 65, No. 3, 01.03.2018, p. 312-316.

Research output: Contribution to journalArticle

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