Diastereoselective synthesis of open-chain secondary alkyllithium compounds and trapping reactions with electrophiles

Guillaume Dagousset, Kohei Moriya, Rasmus Mose, Guillaume Berionni, Paul Knochel

Research output: Contribution to journalArticlepeer-review

Abstract

A practical stereoselective iodide-lithium exchange was used in the first general preparation of functionalized stereodefined acyclic secondary nonstabilized lithium reagents from the corresponding secondary alkyl iodides. These lithium reagents react with various electrophiles including carbon electrophiles with high retention of configuration. Kinetic data on the configurational stability of these acyclic alkyllithium reagents are given. This methodology offers a new entry to chiral synthons for the stereoselective synthesis of open-chain molecules.

Original languageEnglish
Pages (from-to)1425-1429
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number5
DOIs
Publication statusPublished - 27 Jan 2014
Externally publishedYes

Keywords

  • Acylation
  • Diastereoselectivity
  • Kinetics
  • Lithiation
  • Nucleophilic substiution

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