Synthesis of 3-Azabicyclo[ m.2.0] Ring Systems via a Copper-Catalyzed Cascade Reaction of Diazo Compounds with 1, n-Allenynes

J Org Chem. 2020 Mar 20;85(6):4418-4429. doi: 10.1021/acs.joc.0c00149. Epub 2020 Mar 3.

Abstract

A copper-catalyzed cascade reaction of diazo compounds with 1,n-allenynes (n = 6,7) was reported, which provides efficient access to various functionalized 3-azabicyclo[m.2.0] frameworks (m = 5,6) in moderate to excellent yields under mild reaction conditions. The reaction proceeds through intermolecular cross-coupling to form bisallene intermediates, followed by subsequent intramolecular [2+2] cycloaddition.

Publication types

  • Research Support, Non-U.S. Gov't