[4 + 2] Annulation of Donor-Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity

J Org Chem. 2017 Mar 3;82(5):2724-2738. doi: 10.1021/acs.joc.7b00209. Epub 2017 Feb 23.

Abstract

A new process for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.

Publication types

  • Research Support, Non-U.S. Gov't