One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction

Yiwen Xiong, Ping Qian, Chenhui Cao, Haibo Mei, Jianlin Han, Guigen Li, Yi Pan

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

We report here an efficient one-pot method for the synthesis of α,β-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular SN2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1).

Original languageEnglish
Pages (from-to)1802-1807
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
StatePublished - Aug 7 2014

Keywords

  • Aminohalogenation
  • Diamination
  • One-pot
  • Stereoselectivity
  • α,β-diamino ester

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