Diastereoselective Intramolecular [3 + 2]-Annulation of Donor-Acceptor Cyclopropane with Imine-Assembling Hexahydropyrrolo[3,2-c]quinolinone Scaffolds

J Org Chem. 2016 Nov 18;81(22):11185-11194. doi: 10.1021/acs.joc.6b02172. Epub 2016 Nov 3.

Abstract

An intramolecular [3 + 2]-annulation of amide-linked donor-acceptor cyclopropane with in situ-generated imine is described. As a result, diverse hexahydropyrrolo[3,2-c]quinolinones, as the tricyclic core of martinellines, were efficiently assembled in good to excellent yield (up to 93%) with a good diastereomeric ratio (up to 98:2).

Publication types

  • Research Support, Non-U.S. Gov't