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  • Title: Unexpected ring-opening reactions of aziridines with aldehydes catalyzed by nucleophilic carbenes under aerobic conditions.
    Author: Liu YK, Li R, Yue L, Li BJ, Chen YC, Wu Y, Ding LS.
    Journal: Org Lett; 2006 Apr 13; 8(8):1521-4. PubMed ID: 16597100.
    Abstract:
    [reaction: see text] The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene was investigated under aerobic conditions. Unexpected carboxylates of 1,2-amino alcohols from the corresponding aldehydes, rather than the acyl anion ring-opened beta-amino ketones, were exclusively obtained. A plausible mechanism for this unprecedented carbene-mediated reaction was also proposed.
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