(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols

Miguel Peña-López, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

64 Scopus citations

Abstract

A novel strategy for the synthesis of oxazolidin-2-ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C−O and C−N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. While this transformation is already highly chemo- and regioselective, we also developed the first asymmetric version of this method using (R)-(+)-MeO-BIPHEP as the chiral ligand.

Original languageEnglish
Pages (from-to)7826-7830
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume55
Issue number27
DOIs
StatePublished - 27 Jun 2016
Externally publishedYes

Keywords

  • diols
  • domino reactions
  • enantioselectivity
  • oxazolidinones
  • ruthenium catalysis

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