Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones

Reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with various alkyl primary amines gave regio- and stereo-specific [3.2.1]bicyclic α-amino ketones. A detailed mechanism of the reaction was discussed. This reaction was further applied to the preparation of some camphor-derived oxazaborolidines, one of which proved to be an efficient chiral catalyst for the asymmetric borane reduction of prochiral aryl ketones at room temperature.