912581-01-2Relevant academic research and scientific papers
Desymmetrization of cyclohexa-2,5-dienes through a diastereoselective protonation-hydroamination cascade
Lebeuf, Raphael,Robert, Frederic,Schenk, Kurt,Landais, Yannick
, p. 4755 - 4758 (2007/10/03)
(Chemical Equation Presented) Intramolecular hydroamination of cyclohexa-2,5-dienes led with high selectivity to the corresponding bicyclic allylic amines. This study demonstrates that the reaction does not proceed through a direct hydroamination of one of the diastereotopic olefins but more likely involves a diastereoselective protonation of a pentadienyl anion, followed by addition of a lithium amide across the double bond of the resulting 1,3-diene, and is concluded by a highly regioselective protonation of the final allylic anion.
