1370036-07-9Relevant academic research and scientific papers
Furanyl cyclic amines: A diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control
O'Brien, Matthew,Leach, Andrew,Armstrong, Roly J.,Chong, Keting,Sheridan, Ross
, p. 2392 - 2394 (2012/04/23)
Utilising the propensity of the 2-furanyl group to facilitate equilibration of an adjacent tosylamide chiral centre, a diastereoselective route to 2,6-syn-piperidines was developed that proceeds with high levels of thermodynamic stereocontrol. X-ray crystallography structures suggest that, as seen in similar systems, pseudo-allylic strain between the N-tosyl group and the substituents at the 2 and 6 positions dominates stereochemical preference, overriding 1,3 diaxial interactions. The Royal Society of Chemistry 2012.
