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  • Title: Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across alpha-chloro N-sulfinyl ketimines.
    Author: Colpaert F, Mangelinckx S, Leemans E, Denolf B, De Kimpe N.
    Journal: Org Biomol Chem; 2010 Jul 21; 8(14):3251-8. PubMed ID: 20502774.
    Abstract:
    Reaction of chiral alpha-chloro N-tert-butanesulfinyl ketimines with Grignard reagents afforded new chiral N-sulfinyl 2,2-disubstituted aziridines in good to excellent diastereomeric ratio (dr up to 98 : 2). The 1,2,2-trisubstituted aziridines were isolated in high overall yield (51-85%) and with excellent enantiomeric excess (>98% ee). The stereoselectivity obtained in the Grignard addition is rationalized by the coordinating ability of the alpha-chloro atom resulting in the opposite stereochemical outcome as observed for nonfunctionalized N-sulfinyl ketimines.
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