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Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature

  • Shuai Zhu
  • , Mingjie Chen
  • , Haichao Shen
  • , Hanming Ding*
  • , Wenbo Li
  • , Junliang Zhang*
  • *Corresponding author for this work
  • East China Normal University
  • Fudan University

Research output: Contribution to journalArticlepeer-review

Abstract

Metal-catalyzed alkene arylalkoxylation is a powerful complexity-building strategy for the synthesis of oxygen heterocycles from simple γ-unsaturated alcohols, but only a few examples of catalytic enantioselective methods exist. Herein, an efficient palladium-catalyzed enantioselective arylalkoxylation of γ-hydroxyalkenes with aryl halides is reported. The salient features of this transformation include a remarkable broad substrate scope, mild reaction conditions, and good functional group tolerance, delivering a series of chiral tetrahydrofurans containing a tertiary or quaternary stereocenter in good yields with up to 95 % ee. The Xu10 ligand with a suitable side-arm was responsible for the high reactivity and good enantioselectivity of this transformation.

Original languageEnglish
Article number109879
JournalChinese Chemical Letters
Volume35
Issue number11
DOIs
StatePublished - Nov 2024

Keywords

  • Arylalkoxylation
  • Enantioselective
  • Palladium-catalysis
  • Xu-Phos
  • γ-Hydroxyalkenes

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