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Synlett 1998; 1998(7): 754-756
DOI: 10.1055/s-1998-1773
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Scandium-Mediated Opening of Aziridine Carboxylates: A Facile Synthesis of Aryl Substituted Tryptophans

Youssef L. Bennani* , Gui-Dong Zhu, Jennifer C. Freeman
  • *Abbott Laboratories, Metabolic Diseases Research, D4MG, AP10; 100 Abbott Park Rd, Abbott Park, IL 60064-3500, U.S.A.
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Publication Date:
31 December 2000 (online)

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The treatment of enantiomerically pure L-serine-derived N-Cbz- or N-Fmoc-aziridine carboxylates with indole derivatives in the presence of a stoichiometric amount of Sc(Otf)3 in dichloromethane at 0 °C or RT gives the aryl-substituted and protected tryptophan derivatives in good yields. Attempts to catalyze the reaction are also reported.

scandium triflate - aziridine carboxylates - indoles