The First Enantioenriched Metalated Nitrile Possessing Macroscopic Configurational Stability

Abstract

Magnesium−bromine exchange on enantiopure cyclopropyl bromonitrile 5 at −100 °C for 1 min followed by a D2O quench gives the deuterionitrile in 81% ee (retention); additional trapping experiments establish t1/2(rac) = 11.4 h at −100 °C. These experiments provide the first glimpse into the stereochemical aspects of Mg−Br exchange. The intermediate formed is the first metalated nitrile demonstrated to possess macroscopic configurational stability