The first transition metal-ligand complex-catalyzed regioselective and stereoselective aminohalogenation of cinnamic esters

Han Xun Wei, Sun Hee Kim, Guigen Li

Research output: Contribution to journalArticlepeer-review

83 Scopus citations

Abstract

Transition metal-ligand complex-catalyzed regio- and stereoselective aminohalogenation of cinnamic esters has been developed using p-TsNCl2 as the nitrogen and chlorine sources. Dichloro-(1,10-phenanthroline)-palladium (II) as the catalyst can be handled very conveniently due to its property of less hygroscopic as compared with other aminohalogenation catalysts. The reaction is suggested to proceed through the mechanism involving N-tosyl N-chloro aziridinium intermediate. Eight examples are presented with modest to good yields (56-82%) and excellent stereoselectivity (>10:1).

Original languageEnglish
Pages (from-to)3869-3873
Number of pages5
JournalTetrahedron
Volume57
Issue number18
DOIs
StatePublished - Apr 30 2001

Keywords

  • Aminohalogenation
  • Catalysis
  • Haloamine

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