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

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

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Abstract

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
JournalSynthesis
Volume48
Issue number01
Early online date27 Oct 2015
DOIs
Publication statusPublished - Jan 2016

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Keywords

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

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