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

Koichi Mitsudo; Junya Yamamoto; Tomoya Akagi; Atsuhiro Yamashita; Masahiro Haisa; Kazuki Yoshioka; Hiroki Mandai; Koji Ueoka; Christian Hempel; Jun ichi Yoshida; Seiji Suga

doi:10.3762/bjoc.14.100

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

Koichi Mitsudo, Junya Yamamoto, Tomoya Akagi, Atsuhiro Yamashita, Masahiro Haisa, Kazuki Yoshioka, Hiroki Mandai, Koji Ueoka, Christian Hempel, Jun ichi Yoshida, Seiji Suga

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

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	https://doi.org/10.3762/bjoc.14.100
Publication status	Published - May 24 2018

Keywords

Cation pool
Conformation
Electroorganic synthesis
N-acyliminium ion
NMR analysis
Piperidine

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.14.100

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Mitsudo, K., Yamamoto, J., Akagi, T., Yamashita, A., Haisa, M., Yoshioka, K., Mandai, H., Ueoka, K., Hempel, C., Yoshida, J. I., & Suga, S. (2018). 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. Beilstein Journal of Organic Chemistry, 14, 1192-1202. https://doi.org/10.3762/bjoc.14.100

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 › peer-review

Mitsudo, K, Yamamoto, J, Akagi, T, Yamashita, A, Haisa, M, Yoshioka, K, Mandai, H, Ueoka, K, Hempel, C, Yoshida, JI & Suga, S 2018, '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', Beilstein Journal of Organic Chemistry, vol. 14, pp. 1192-1202. https://doi.org/10.3762/bjoc.14.100

Mitsudo K, Yamamoto J, Akagi T, Yamashita A, Haisa M, Yoshioka K et al. 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. Beilstein Journal of Organic Chemistry. 2018 May 24;14:1192-1202. https://doi.org/10.3762/bjoc.14.100

Mitsudo, Koichi ; Yamamoto, Junya ; Akagi, Tomoya ; Yamashita, Atsuhiro ; Haisa, Masahiro ; Yoshioka, Kazuki ; Mandai, Hiroki ; Ueoka, Koji ; Hempel, Christian ; Yoshida, Jun ichi ; Suga, Seiji. / 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: Beilstein Journal of Organic Chemistry. 2018 ; Vol. 14. pp. 1192-1202.

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title = "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",

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{\textquoteright}s hypothesis.",

keywords = "Cation pool, Conformation, Electroorganic synthesis, N-acyliminium ion, NMR analysis, Piperidine",

author = "Koichi Mitsudo and Junya Yamamoto and Tomoya Akagi and Atsuhiro Yamashita and Masahiro Haisa and Kazuki Yoshioka and Hiroki Mandai and Koji Ueoka and Christian Hempel and Yoshida, {Jun ichi} and Seiji Suga",

note = "Funding Information: This work was supported in part by JSPS KAKENHI (No. 16H01155, No. 16K05777), and by JST, ACT-C, Japan.",

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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

N1 - Funding Information: This work was supported in part by JSPS KAKENHI (No. 16H01155, No. 16K05777), and by JST, ACT-C, Japan.

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

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