A Convenient Synthesis of γ-Hydroxy and γ-Keto Nitriles

Abstract

γ-Hydroxy nitriles are convenient intermediates in the preparation of γ-keto nitriles. However they are not obtained easily. Indeed, the reaction of an α-metalated nitrile with an epoxide does not give the suitable results; in some cases authors have observed the formation of a lactone only (1), but generally it is a mixture of hydroxy nitrile 1, cyclic iminoether 2 and lactone 3 which is obtained (2). Only intramolecular reactions afford the expected hydroxy nitriles (3).