A stereoselective route towards vinyl-substituted lactams will be presented. This reaction uses an inter-converting mixture of allylic azides, which are subjected to intramolecular Schmidt reaction to afford the desired products.  The scope of the reaction and source of its stereoselectivity has been studied from experimental and computational perspectives. Its application towards the synthesis of pinnaic acid will be discussed.

Combined allylic azide rearrangement and intramolecular Schmidt reaction

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.