Palladium-Catalyzed Reductive Cleavage of 3-Substituted 2-[(E)-2-(Alkoxycarbonyl)ethenyl]aziridines with Formic Acid

Akiharu Satake; Isao Shimizu; Akio Yamamoto

doi:10.1055/s-1995-4876

Synlett 1995; 1995(1): 64-68
DOI: 10.1055/s-1995-4876

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Palladium-Catalyzed Reductive Cleavage of 3-Substituted 2-[(E)-2-(Alkoxycarbonyl)ethenyl]aziridines with Formic Acid

Akiharu Satake, Isao Shimizu^* , Akio Yamamoto

^*Department of Applied Chemistry, School of Science and Engineering, Waseda University, Okubo 3-4-1, Shinjuku-ku, Tokyo 169

Abstract

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Reductive cleavage of 2-alkenylaziridines having an N-substituent such as a Ts or Boc group with formic acid to unsaturated amines proceeds in the presence of palladium catalyst. Whereas α,β-unsaturated δ-amino esters are obtained selectively in the reaction of 3-substituted 2-[2-(alkoxycarbonyl)ethenyl]-1-[(tert-butyloxy)carbonyl] aziridines in acetonitrile, β,γ-unsaturated δ-amino esters are obtained as major products by S_N2’ inversion in DMSO in the presence of maleic anhydride or dimethyl acetylenedicarboxylate.

palladium catalyst - aziridine - reductive cleavage - formic acid - peptide isoster

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