Acylative kinetic resolution of alcohols using a recyclable polymer-supported isothiourea catalyst in batch and flow

Rifahath Neyyappadath, Ross Chisholm, Mark David Greenhalgh, Carles Rodriguez-Escrich, Miquel A. Pericàs, Georg Hähner, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)
3 Downloads (Pure)

Abstract

A polystyrene-supported isothiourea catalyst, based on the homogeneous catalyst HyperBTM, has been prepared and used for the acylative kinetic resolution of secondary alcohols. A wide range of alcohols, including benzylic, allylic and propargylic alcohols, cycloalkanol derivatives and a 1,2-diol, has been resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s up to 622). The catalyst can be recovered and reused by a simple filtration and washing sequence, with no special precautions needed. The recyclability of the catalyst was demonstrated (15 cycles) with no significant loss in either activity or selectivity. The recyclable catalyst was also used for the sequential resolution of 10 different alcohols us-ing different anhydrides with no cross-contamination between cycles. Finally, successful application in a continuous flow process demonstrated the first example of an immobilized Lewis base catalyst used for the kinetic resolution of alcohols in flow.
Original languageEnglish
Pages (from-to)1067-1075
Number of pages9
JournalACS Catalysis
Volume8
Issue number2
Early online date21 Dec 2017
DOIs
Publication statusPublished - 2 Feb 2018

Keywords

  • Kinetic resolution
  • Isothioureas
  • Lewis base catalysis
  • Polymer-supported catalysts
  • Catalyst recyclability
  • Acyl transfer reactions
  • Enantioselective catalysis
  • Continuous flow

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