Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate

Abstract

A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones. © 2010 Elsevier Ltd. All rights reserved.