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Paper | Special issue | Vol 37, No. 1, 1994, pp.461-475
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S34
Enantiomerically Pure β-Amino Sulfides amd β-Amino Thiols from Ephedrine

Martin A. Poelert, Robert P. Hof, Nathalie C. M. W. Peper, and Richard M. Kellogg*

*Department of Organic and Molecular, Inorganic Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherland


Ephedrine and pseudoephedrine are converted by means of a Mitsunobu reaction to respectively trans- and cis-aziridines, which can be ringopened at the benzylic center with inversion of configuration by thiols and thiol acids. The trans-aziridine from ephedrine reacts also with H2S in acetone under which conditions the amino thiol is trapped as the thiazolane. The same aziridine also undergoes cycloaddition with CS2.