N-amination using N-methoxycarbonyl-3-phenyloxaziridine. Direct access to chiral N β-protected α-hydrazinoacids and carbazates

J Vidal, J Drouin, A Collet

Index: Vidal, Joelle; Drouin, Jacques; Collet, Andre Journal of the Chemical Society, Chemical Communications, 1991 , # 6 p. 435 - 437

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Citation Number: 14

Abstract

We report that the new compound N-methoxycarbonyl-3- phenyloxaziridine 1 is an exceptionally mild and efficient reagent for the conversion of most primary and secondary amines :NH to the corresponding carbazates :N- NHC02Me. We could prepare oxaziridine 1 in multigram quantities by controlled oxidation+ of the N-methoxycarbonyl imino deriva- ... $ Oxaziridine 1: IH NMR (CDCl3, 27 "C, slow cisltrans equilibrium): the trans structure was assigned to the major ...