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Nucleophilic addition of organometallic reagents to cinchona alkaloids: Simple access to diverse architectures

  • RWTH Aachen University

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

(Chemical Equation Presented) Aminal pharm: Grignard reagents undergo a surprising nucleophilic aromatic addition reaction to cinchona alkaloids to stereoselectively produce cyclic aminals. Structurally diverse alkaloid derivatives with rigid cores that bear reactive functional groups (see examples) can be readily synthesized by this simple nucleophilic alkylation protocol.

Original languageEnglish
Pages (from-to)5164-5167
Number of pages4
JournalAngewandte Chemie International Edition in English
Volume46
Issue number27
DOIs
StatePublished - 2007
Externally publishedYes

Keywords

  • Cinchona alkaloids
  • Grignard reaction
  • Heterocycles
  • Neighboring-group effects
  • Nucleophilic addition

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