Engineering polymer-enhanced bimetallic cooperative interactions in the hydrolytic kinetic resolution of epoxides

Xiaolai Zheng, Christopher W. Jones, Marcus Weck

Research output: Contribution to journalArticlepeer-review

Abstract

Through systematic variations of the length of oligo(ethylene glycol)-based linkers and the catalyst density of poly(styrene)-supported cobalt-salen catalysts, we have elucidated an optimal catalyst flexibility and density of polymeric Co-salen catalysts for the hydrolytic kinetic resolution (HKR) of racemic terminal epoxides that follows a bimetallic cooperative pathway. The optimized polymeric catalyst brings the two cooperative Co-salen units to a favorable proximity efficiently and hence displays significantly improved catalytic performance in the HKR compared with its monomeric small molecule analogue. Complex Co(5b), representing the most active poly(styrene)-supported HKR catalyst known so far, can effect the resolution of a variety of epoxides to reach ≥ 98 % ee in 6-24 h with a low cobalt loading of 0.01-0.1 mol%.

Original languageEnglish (US)
Pages (from-to)255-261
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number2
DOIs
StatePublished - Jan 2008

Keywords

  • Asymmetric catalysis
  • Cobalt
  • Hydrolytic kinetic resolution
  • Poly(styrene)
  • Salen ligands

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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