244263-35-2Relevant academic research and scientific papers
A highly enantioselective organocatalytic method for reduction of aromatic N-alkyl ketimines
Wang, Chao,Wu, Xinjun,Zhou, Li,Sun, Jian
supporting information; experimental part, p. 8789 - 8792 (2009/09/25)
A study has demonstrated the development of a highly enantioselective catalytic method for the reduction of aromatic N-alkyl ketimines by trichlorosilane under mild conditions using the newly designed Lewis base organocatalyst that incorporates C- and S-chirality. The S-chiral sulfinamide group in these catalysts plays a crucial role similar to the carboxamide groups as Lewis base for the activation of HSiCl3, and also serves as a source of chirality that the carboxamide group lacks for the asymmetric induction. The results of the study showed that excellent enantioselectivities of up to 99.6% ee and high yields were obtained for a wide range of substrates. Further works is also in progress to clarify the mechanism of the transformation and explore the full application scope of the present catalyst system.
A concise route to novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexanes
Piotrowski, David W.
, p. 1091 - 1093 (2007/10/03)
A number of novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexane derivatives were prepared by an intramolecular [2+2] photocycloaddition in the presence of acetophenone as the sensitizer. Substitution of the azabicyclo[2.1.1]hexane ring was accomplished by appropriate choice of the heteroaryl ketone and allylamine starting materials. Several aryl 9a-e, g and pyridyl analogs 9h-l were prepared by this method. The structures of 9a and 9i were verified by X-ray crystallography. Several of the photoproducts 9 were converted into the corresponding N-Me and N-H 2,4-methanonicotine analogs 4 by reduction or hydrolysis of the N-carboethoxy group.
