TY - JOUR A1 - Mitsudo, Koichi A1 - Yamamoto, Junya A1 - Akagi, Tomoya A1 - Yamashita, Atsuhiro A1 - Haisa, Masahiro A1 - Yoshioka, Kazuki A1 - Mandai, Hiroki A1 - Ueoka, Koji A1 - Hempel, Christian A1 - Yoshida, Jun-ichi A1 - Suga, Seiji T1 - 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 JF - Beilstein Journal of Organic Chemistry PY - 2018/// VL - 14 SP - 1192 EP - 1202 SN - 1860-5397 DO - 10.3762/bjoc.14.100 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.14.100 KW - cation pool KW - conformation KW - electroorganic synthesis KW - N-acyliminium ion KW - NMR analysis KW - piperidine N2 - 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. ER -