Chelation-controlled asymmetric aminohalogenation reaction

Yi Ning Wang, Adiseshu Kattuboina, Teng Ai, Diya Banerjee, Guigen Li

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The chelation-controlled asymmetric aminohalogenation of α,β-unsaturated 3-aryl-N-acyl-N-4-phenyl-2-oxazolidinones have been established by using palladium(II) acetate as the catalyst and as the chelation metal. The reaction is very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide and catalyst together with 4 Å molecular sieves at rt in any convenient vial of appropriate size without special protection from inert gases. Unlike the previous asymmetric aminohalogenation, the ionic liquid, [BMIM][NTf2], was found to be superior to [BMIM][BF4] as the reaction media. It was also found that palladium(II) acetate has to be used together with 1 equiv of MeCN to achieve the opposite chelation control. The resulting absolute stereochemistry of the product was unambiguously determined by X-ray structural analysis.

Original languageEnglish (US)
Pages (from-to)7894-7898
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number44
DOIs
StatePublished - Oct 29 2007

Bibliographical note

Funding Information:
We gratefully acknowledge the Robert A. Welch foundation (D-1361) for its generous support of this work. We thank Mr. David W. Purkiss for his assistance in NMR analysis and Eileen Duesler (University of New Mexico) for assistance in X-ray analysis.

Keywords

  • 4-Phenyl-2-oxazolidinone
  • Aminohalogenation
  • Ionic liquids
  • Palladium(II) acetate

Fingerprint

Dive into the research topics of 'Chelation-controlled asymmetric aminohalogenation reaction'. Together they form a unique fingerprint.

Cite this