Easy preparation of enantiopure C@2# symmetrical hydroxy and amino sulfides devired from ephedrine and their application in a Pd catalyzed coupling reaction

Bartjan Koning, Ron Hulst, Richard M. Kellogg

    Research output: Contribution to journalArticleAcademicpeer-review

    17 Citations (Scopus)

    Abstract

    Ephedrine can be readily converted by means of intramolecular SN2 substitution by the hydroxyl or amino substituent into, respectively, the corresponding epoxide or aziridine with high stereocontrol. Subsequent stereoselective ring opening at the benzylic centre using tetrabutyl‐ammonium fluoride (TBAF) and dithiols affords the C2 symmetrical hydroxy or amino sulfides in excellent yield. Application of these ligands in a palladium‐catalyzed asymmetric allylic substitution reaction gave moderate to high enantiomeric excesses (up to 79%) and high yields of product.
    Original languageEnglish
    Pages (from-to)49-55
    Number of pages7
    JournalRecueil des travaux chimiques des Pays-Bas
    Volume115
    Issue number1
    DOIs
    Publication statusPublished - 1996

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