Conjugate Additions of Amines to Maleimides via Cooperative Catalysis

Brice E. Uno, Kristine K. Deibler, Carlos Villa, Arjun Raghuraman, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A cooperative system comprising of a lithium Lewis acid and amine base significantly enhances the rate of the conjugate addition of a wide array of amines to maleimides. This operationally simple, scalable method provides mono-addition products in high yields and purity. This conjugation was successfully applied to the kinase inhibitor crizotinib in a chemoselective ligation to create novel fluorescent probe. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)1719-1725
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number8
DOIs
StatePublished - Apr 17 2018

Keywords

  • amino-conjugate addition
  • bioconjugation
  • cooperative catalysis
  • crizotinib
  • maleimide
  • synergistic catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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