Synthesis of Azide-Containing Cyclopentenes

  • Author: Angewandte Chemie International Edition
  • Published Date: 03 June 2017
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Synthesis of Azide-Containing Cyclopentenes

Vinyldiazo compounds and vinylazides show a rich chemistry and have many applications in organic synthesis. In general, in the presence of a transition metal, both types of reagents undergo a facile nitrogen extrusion together with the generation of a highly reactive species.

Enol López and Luis A. López, Universidad de Oviedo, Spain, have found suitable conditions for a copper(I)-promoted selective cyclization reaction of stabilized vinyldiazo compounds with vinylazides, despite the presence of multiple reactive sites in both reagents. In particular, the use of a readily available copper complex enabled the synthesis of cyclopentene derivatives while retaining the azide group (product pictured). The process involves an initial cyclization reaction and a subsequent migration of the azide group.

The reaction has a broad substrate scope and proceeds in good to excellent yields. The presence of the azide function in the final products provides a variety of synthetic opportunities.


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