Previous Article in event
Next Article in event
Enantiospecific Preparation of 10-(pyperidin-1-yl)Camphor: A Model Procedure for 10-Aminocamphors
Published: 01 November 2004 by MDPI in The 8th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
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.