1029440-72-9Relevant academic research and scientific papers
Chiral bicyclic imidazolium salts as a new class of N-heterocyclic carbene precursors
Matsuoka, Yuki,Ishida, Yasuhiro,Saigo, Kazuhiko
, p. 2985 - 2989 (2008/09/20)
A N(1)-C(5) bridged chiral bicyclic imidazole with a morpholine framework was synthesized from an enantiopure 2-amino alcohol. The resultant imidazole reacted with various electrophiles, including primary and secondary alkyl halides, benzyne, and an electron-deficient aryl halide, to give the corresponding imidazolium salts. Some of the imidazolium salts were found to have potential as the precursor of a chiral N-heterocyclic carbene catalyst; by the direct annulation of an enal and a ketone through the intermediacy of a homoenolate and an activated carboxylate, the target lactone was obtained in an enantiomerically enriched form (up to 66% ee).
