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Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim
  • , Gwanggyun Kim
  • , Doyoon Kim
  • , Jun Hee Lee*
  • , Seung Hwan Cho*
  • *Corresponding author for this work
  • Pohang University of Science and Technology
  • Dongguk University

Research output: Contribution to journalReview articlepeer-review

Abstract

The transition-metal-catalyzed asymmetric allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction. Particularly, the generation and utilization of chiral secondary alkylcopper species have received considerable attention due to their unique properties in stereoselective allylic substitution. This review highlights recent advances in copper-catalyzed asymmetric allylic substitution reactions with chiral secondary alkylcopper species, encompassing several key strategies for their generation: stereospecific transmetalation of organolithium and organoboron compounds, copper hydride catalysis, and enantiotopic-group-selective transformations of 1,1-diborylalkanes. Detailed mechanistic insights into stereochemical control and current challenges in this field are also discussed.

Original languageEnglish
Pages (from-to)639-658
Number of pages20
JournalBeilstein Journal of Organic Chemistry
Volume21
DOIs
StatePublished - 2025

Keywords

  • allylic substitution
  • chiral secondary organocopper
  • copper-mediated reaction
  • stereoselectivity

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