Wagner Meerwein rearrangement of [3.3.1] bicyclic N-Boc aminols: vinyl migration in preference to aryl migration

The Wagner-Meerwein rearrangement of [3.3.1] bicyclic N-Boc aminols was established, featuring the migration of the vinyl group instead of the aromatic ring. The structure of the rearrangement product was deduced through extensive spectroscopic studies and confirmed by the synthetic efforts. The scope of the reaction was examined and reasonably good yields were obtained for substrates with alkyl, allyl or benzyl substituent. (C) 2014 Elsevier Ltd. All rights reserved.