A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4‑Substituted 3‑Azabicyclo[3.1.0]hexan-2-ones from 2‑Iodo­cyclo­propane­carboxamides

Carné-Carnavalet, Benoît de; Meyer, Christophe; Cossy, Janine; Folléas, Benoît; Brayer, Jean-Louis; Demoute, Jean-Pierre

doi:10.1021/jo400713u.s001

A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4‑Substituted 3‑Azabicyclo[3.1.0]hexan-2-ones from 2‑Iodocyclopropanecarboxamides

journal contribution

posted on 2013-06-07, 00:00 authored by Benoît de Carné-Carnavalet, Christophe Meyer, Janine Cossy, Benoît Folléas, Jean-Louis Brayer, Jean-Pierre Demoute

A variety of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones have been prepared from 2-iodocyclopropanecarboxamides by a three-step sequence involving a copper-free Sonogashira coupling with terminal aryl- or heteroarylalkynes, followed by a 5-exo-dig cyclization and an ionic hydrogenation.