Copper-Catalyzed Ring Expansion of Vinyl Aziridines under Mild Conditions

Eleonora Tosi (1) , Kim Spielmann (1) , Renata Marcia de Figueiredo (1) , Jean-Marc Campagne (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

Vinyl aziridines are versatile starting materials toward ring expansion transformations. Such processes are widely used to give various medium or larger N-heterocycles of synthetic interest. This letter describes a copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines by using a Cu(I) salt [(CuOTf)2·toluene or Cu(MeCN)4·PF6]. In particular, this transformation occurs under mild conditions (THF, rt).

Mots clés: ring-expansion; vinyl aziridines; pyrrolines; copper catalysis; heterocycles

Domaines: Chimie organique

Eleonora Tosi, Kim Spielmann, Renata Marcia de Figueiredo, Jean-Marc Campagne. Copper-Catalyzed Ring Expansion of Vinyl Aziridines under Mild Conditions. SYNLETT, 2021, 32, pp.517-520. ⟨10.1055/s-0040-1706007⟩. ⟨hal-03165251⟩