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Benoît de Carné-Carnavalet, Alexis Archambeau, Dr. Christophe Meyer, Prof. Dr. Janine Cossy, Dr. Benoît Folléas, Dr. Jean-Louis Brayer and Dr. Jean-Pierre Demoute Efficient Synthesis of Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides Using a Copper-Free Sonogashira Coupling Chemistry - A European Journal 18

Article first published online: 23 NOV 2012 | DOI: 10.1002/chem.201203153

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A copper-free Sonogashira coupling between cis-2-iodocyclopropanecarboxamides and terminal aryl-, heteroaryl-alkynes or enynes followed by 5-exo-dig cyclization provides an efficient access to substituted 4-methylene-3-azabicyclo[3.1.0]hexan-2-ones (see scheme). Protonation of these enamides generates N-acyliminium ions, which can be involved in Pictet–Spengler cyclizations leading to new 3-azabicyclo[3.1.0]hexan-2-ones containing a quaternary stereocenter at C4 with high diastereoselectivities.

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