Selective elaboration of aminodiols towards small ring α- and β-amino acid derivatives that incorporate an aziridine, azetidine, or epoxide scaffold

The osmium-catalyzed dihydroxylation of N-substituted alkyl 2-(aminomethyl) acrylates resulted in the efficient synthesis of 2-(aminomethyl)-2,3-dihydroxypropanoates in good yields (82-89 %). The resulting aminodiols were elaborated in a selective diversity-oriented synthesis to produce the corresponding 2-(aminomethyl) oxirane-2-carboxylates, functionalized aziridine-2-carboxylates, and azetidine-3-carboxylates by using straightforward reactions.

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