Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 1192-1202 |
| Number of pages | 11 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 14 |
| DOIs | |
| Publication status | Published - May 24 2018 |
Fingerprint
Keywords
- Cation pool
- Conformation
- Electroorganic synthesis
- N-acyliminium ion
- NMR analysis
- Piperidine
ASJC Scopus subject areas
- Organic Chemistry
Cite this
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. / Mitsudo, Koichi; Yamamoto, Junya; Akagi, Tomoya; Yamashita, Atsuhiro; Haisa, Masahiro; Yoshioka, Kazuki; Mandai, Hiroki; Ueoka, Koji; Hempel, Christian; Yoshida, Jun ichi; Suga, Seiji.
In: Beilstein Journal of Organic Chemistry, Vol. 14, 24.05.2018, p. 1192-1202.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoselective nucleophilic addition reactions to cyclic n-acyliminium ions using the indirect cation pool method
T2 - Elucidation of stereoselectivity by spectroscopic conformational analysis and dft calculations
AU - Mitsudo, Koichi
AU - Yamamoto, Junya
AU - Akagi, Tomoya
AU - Yamashita, Atsuhiro
AU - Haisa, Masahiro
AU - Yoshioka, Kazuki
AU - Mandai, Hiroki
AU - Ueoka, Koji
AU - Hempel, Christian
AU - Yoshida, Jun ichi
AU - Suga, Seiji
PY - 2018/5/24
Y1 - 2018/5/24
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.
AB - 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.
KW - Cation pool
KW - Conformation
KW - Electroorganic synthesis
KW - N-acyliminium ion
KW - NMR analysis
KW - Piperidine
UR - http://www.scopus.com/inward/record.url?scp=85047725259&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85047725259&partnerID=8YFLogxK
U2 - 10.3762/bjoc.14.100
DO - 10.3762/bjoc.14.100
M3 - Article
AN - SCOPUS:85047725259
VL - 14
SP - 1192
EP - 1202
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -