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Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3‑Substituted Oxindoles

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posted on 18.12.2013 by Kohsuke Ohmatsu, Yuichiro Ando, Takashi Ooi
A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon–carbon bond formation through direct substitution at the tetrasubstituted chiral carbon.