Synthesis of new derivatives from a Tröger base via exchange of the methano bridge with carbonyl compounds

Abstract

A simple one-pot method has been developed for the preparation of new Tröger base derivatives by an exchange reaction with the methano bridge of rac-Tröger base derivatives with carbonyl compounds in the presence of TiCl 4 or POCl 3. The use of chiral (S,S)-N,N-bis(α- methylbenzyl)formamide as a carbonyl compound gave the corresponding methano Tröger base derivatives with the diastereomeric ratios of up to 77:23. © 2012 Elsevier Ltd. All rights reserved.