Tetrahedron

Acyl migration from N to C in aziridine-2-carboxylic esters

B Strumfs, J Hermane, S Belyakov, P Trapencieris

Index: Strumfs, Boriss; Hermane, Jekaterina; Belyakov, Sergey; Trapencieris, Peteris Tetrahedron, 2014 , vol. 70, # 2 p. 355 - 362

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Citation Number: 2

Abstract

Because N to C carboxyl migration is precedented in acyclic amino acid derivatives, 25 and is known with 2-lithioaziridines that lack the stabilizing 2-alkoxycarbonyl group, 21 and 23 it might also occur with aziridine enolates. If the relatively strained bicyclic transition state for migration is accessible below the decomposition temperature, then a convenient synthesis of 2-substituted aziridine carboxylates may be possible from stable, readily available precursors.