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Regio- and Stereoselective C-2 and C-3 Cleavage of 2-(1-Aminoalkyl)aziridines with Alcohols, Carboxylic Acids, and Sodium Iodide

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journal contribution
posted on 28.10.2003, 00:00 by José M. Concellón, Estela Riego, José Ramón Suárez
Ring opening of nonactivated aziridines 1 using several nucleophiles, such as alcohols, carboxylic acids, and sodium iodide, is described. Depending on the nucleophile used, aziridines 1 are cleaved at C-3 or C-2 with total regio- and stereoselectivity, affording chiral 2-alkoxy-1,3-diamines 2 with alcohols, or O-acylated-1-hydroxy-2,3-diamines 6 with carboxylic acids in moderate or high yield. In the case of the aziridines derived from phenylalanine, treatment with NaI afford trans-4-phenylbut-3-en-1,2-diamines 9, generating the alkene with total diastereoselectivity. Mechanisms have been proposed to explain these reactions.