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Enantiospecific Preparation of 10-(pyperidin-1-yl)Camphor: A Model Procedure for 10-Aminocamphors
1 , 2 , 2 , 2 , * 1
1  Universidad Complutense de Madrid, Departamento de Química Orgánica I, Ciudad Universitaria s/n, 28040 Madrid, Spain
2  Universidad Nacional de Educación a Distancia, Senda del Rey 9, 28040 Madrid, Spain

Abstract: Enantiopure (1R)-10-(pyperidin-1-yl)camphor has been straightforwardly obtained from natural camphor in five individual steps and with a high overall yield. The process involves a stereocontrolled double-Wagner-Meerwein-rearrangement strategy to generate 10-(triflyloxy)camphor as the key intermediate. This peculiarly-stable neopentylic-like triflate is able to react with pyperidine easily and without producing Grob-like fragmentation of the b-(triflyloxy)ketone-based norbornane system. The described procedure constitutes a model procedure for the sterecontrolled preparation of interesting 10-aminocamphors.
Keywords: n/a