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Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines

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journal contribution
posted on 10.10.2007, 00:00 by Emily B. Rowland, Gerald B. Rowland, Edwin Rivera-Otero, Jon C. Antilla
The enantioselective ring-opening of meso-aziridines with azide nucleophiles proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ.