N-Acyliminium Intermediates in Solid-Phase Synthesis

Sebastian Thordal le Quement, Rico Petersen, M. Meldal, Thomas Eiland Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

N-Acyliminium ions are powerful intermediates in synthetic organic chemistry. Examples of their use are numerous in solution-phase synthesis, but there are unmerited few reports on these highly reactive electrophiles in solid-phase synthesis. The present review covers the literature to date and illustrates the methods used to generate N-acyliminitun intermediates on solid support and their further elaboration to a range of pharmacologically interesting peptidomimetics, heterocycles, and other small molecules.
Original languageEnglish
JournalBiopolymers
Volume94
Issue number2
Pages (from-to)242-256
ISSN0006-3525
DOIs
Publication statusPublished - 2010

Keywords

  • Pictet-Spengler reaction
  • peptidomimetics
  • heterocycles
  • solid-phase synthesis
  • N-acyliminium ion

Cite this

Quement, S. T. L., Petersen, R., Meldal, M., & Nielsen, T. E. (2010). N-Acyliminium Intermediates in Solid-Phase Synthesis. Biopolymers, 94(2), 242-256. https://doi.org/10.1002/bip.21358