Synthesis and determination of the absolute stereochemistry of the enantiomers of adrafinil and modafinil

Antonio Osorio-Lozada, Thomas Prisinzano, Horacio F. Olivo

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Both enantiomers of modafinil, adrafinil, modafinic acid and ethyl modafinate were prepared from the diastereomers formed by reacting racemic β-sulfinyl carboxylic acid with (4R)-phenyl-thiazolidinethione. The absolute stereochemistry of the sulfoxide group was confirmed via X-ray analysis of one of the thiazolidinethione diastereomers.

Original languageEnglish
Pages (from-to)3811-3815
Number of pages5
JournalTetrahedron Asymmetry
Volume15
Issue number23
DOIs
StatePublished - Nov 29 2004

Bibliographical note

Funding Information:
Financial support for this work was provided by the National Science Foundation (CHE-0111292 and EEC-0310689). We thank Mr. John Podobinski for the preparation of compound 4 and Dr. Dale Swenson for obtaining the crystallographic analysis of compound (−)- 5 . We are indebted to Dr. Blake Watkins (University of Mississippi) for obtaining all the HRMS.

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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