We have investigated several factors affecting stereoselectivity in the aza-Cope rearrangement�Mannich cyclizations of conformationally mobile iminium cations.  In the course of these studies, we have found that iminium cations formed by treating the corresponding oxazolidine with a Lewis acid result in more diastereoselective reactions than those where a Bronsted acid is used or those in which the iminium cation is generated via condensation with an aldehyde.  The results of theoretical investigations of these selectivity differences and the application of the aza-Cope Mannich reaction to the synthesis of unnatural amino acids will be presented.  

Diastereoselectivity in the aza-Cope rearrangement—Mannich cyclization of conformationally mobile iminium cations

239th National Meeting (2010)

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