Preparative Organic Chemistry
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ChemInform Abstract: Nucleophilic Substitutions Using O-Alkyl-N,N′-dialkylisoureas. Applications to Ephedrines.
First published: February 7, 1995
Abstract
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ChemInform Abstract
Treatment of the isourea (I) with benzothioic acid followed by reduction gives the thiol (II) with inversion of configuration. On the other hand the isoureas (V) resulting from the ephidrines (III) undergo substitution with retention of configuration, probably by a double inversion pathway via aziridinium ion intermediates.
