Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine

Wayne W. Harding, Matthis Hodge, Zhixia Wang, William L. Woolverton, Damon Parrish, Jeffrey R. Deschamps, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.

Original languageEnglish
Pages (from-to)2249-2256
Number of pages8
JournalTetrahedron Asymmetry
Issue number13
StatePublished - Jul 4 2005

Bibliographical note

Funding Information:
The authors (W.W.H., T.E.P.) thank the Biological Sciences Funding Program of the University of Iowa and (W.L.W.) the National Institute on Drug Abuse for financial support. W.L.W. is a recipient of National Institute on Drug Abuse grant K05-DA15343. The X-ray crystallographic work was supported in part by the National Institute on Drug Abuse, NIH, DHHS, and the Office of Naval Research. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa for mass spectral analysis.

ASJC Scopus subject areas

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


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