Synthesis of Isoindoles from Intramolecular Condensation of Benzyl Azides with α-Aryldiazoesters

J Org Chem. 2019 May 3;84(9):5813-5820. doi: 10.1021/acs.joc.8b03180. Epub 2019 Apr 1.

Abstract

Rh-catalyzed intramolecular condensation of the benzyl azides with α-aryldiazoesters was explored. The reaction proceeded through the nucleophilic attack of the organic azide onto a rhodium carbenoid, while releasing nitrogen gas, affording the α-imino esters as the primary product. Tautomerization of the imino esters efficiently gave 13 desired isoindoles with good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't