Stereospecific diaza-cope rearrangement driven by steric strain

Abstract

(Chemical Equation Presented) Bucklingunder the strain: Steric strain was used to drive the diaza-Cope rearrangement to completion (see scheme) with a high degree of stereospecificity (>99.5% ee), as evidenced by chiral-phase HPLC and crystal data. There is good agreement between the experimental and computational values for the rate and equilibrium constants for the rearrangement. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.