243655-94-9Relevant articles and documents
About the Leuckart reaction of chiral 2-norbornanones bearing electron-withdrawing groups: Reaction of bridgehead triflates and triflamides
García Martínez, Antonio,Teso Vilar, Enrique,García Fraile, Amelia,Martínez-Ruiz, Paloma
, p. 1565 - 1569 (2003)
The mechanism of the Leuckart reaction of 3,3- and 7,7-dimethyl-2-oxo-1-norbornyl triflates and triflamides, synthesised by us starting from (1R)-camphor and (1R)-fenchone, has been studied. Strikingly, the electron-withdrawing capacity of the bridgehead substituents has demonstrated not to be enough to control the Wagner-Meerwein rearrangement during the course of the reaction, so that only both enantiomers of a 3,3-dimethylnorbornanediamine derivative have been obtained as final products. As a result, the total synthesis of these interesting chiral compounds has been optimised and shortened until three overall steps starting from (1R)-fenchone.