Asymmetric Synthesis and Absolute Configuration of (+)- and (–)-Perhexiline

Chih-Chung Tseng, Iain R. Greig, William T. A. Harrison, Matteo Zanda

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6 Citations (Scopus)
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Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (–)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (–)-S/(+)-R absolute stereochemistry by X-ray crystallography.
Original languageEnglish
Pages (from-to)73-78
Number of pages6
Issue number01
Early online date27 Oct 2015
Publication statusPublished - Jan 2016

Bibliographical note

We gratefully thank Signal Pharma for financial support and fellowship (C.C.T), and the EPSRC National Mass Spectrometry Service Centre (Swansea, UK) for performing HRMS analyses. We thank Prof Michael Frenneaux (University of East Anglia, Norwich, UK) for useful and stimulating discussions.


  • perhexiline
  • asymmetric analysis
  • stereochemistry
  • medicinal chemistry
  • crystal structure


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