Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations

In this study, six-membered N-acyliminium ions were generated by the “indirect cation pool” method and reacted with several nucleophiles. These reactions afforded disubstituted piperidine derivatives with high diastereoselectivities and good to excellent yields. The conformations of the obtained N-a...

Descripción completa

Detalles Bibliográficos
Autores principales: Mitsudo, Koichi, Yamamoto, Junya, Akagi, Tomoya, Yamashita, Atsuhiro, Haisa, Masahiro, Yoshioka, Kazuki, Mandai, Hiroki, Ueoka, Koji, Hempel, Christian, Yoshida, Jun-ichi, Suga, Seiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009180/
https://www.ncbi.nlm.nih.gov/pubmed/29977386
http://dx.doi.org/10.3762/bjoc.14.100
Descripción
Sumario:In this study, six-membered N-acyliminium ions were generated by the “indirect cation pool” method and reacted with several nucleophiles. These reactions afforded disubstituted piperidine derivatives with high diastereoselectivities and good to excellent yields. The conformations of the obtained N-acyliminium ions were studied by low temperature NMR analyses and DFT calculations and were found to be consistent with the Steven’s hypothesis.

Ejemplares similares