Synthesis of Allylic Hydroxyenamines for Oxaza-Cope Rearrangement Reactions

Synthesis of stereochemically defined bioactive natural products containing a nitrogen moiety has fostered substantial attention from the synthetic community. However, existing methods of synthesizing the vicinal stereocenters present in these natural products are limited and have thus restrained the pace of production of these very important potential drug molecules. The work described herein seeks to combat these retardation factors by providing a simpler way to assemble these challenging chemical motifs by proceeding through a convergent coupling reaction with subsequent [3,3]-sigmatropic rearrangement to forge new stereocenters. The reaction aims to modify and improve synthetic utility of the esteemed Cope rearrangement and some of its isolobal variants which are distinguished for tolerating significant steric hindrance.