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 journalArticle

2 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 languageEnglish
Pages (from-to)1192-1202
Number of pages11
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - May 24 2018

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Stereoselectivity
Addition reactions
Spectroscopic analysis
Cations
Ions
Nucleophiles
Discrete Fourier transforms
Conformations
Nuclear magnetic resonance
Derivatives
Temperature
piperidine

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 journalArticle

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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AU - Akagi, Tomoya

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AU - Yoshioka, Kazuki

AU - Mandai, Hiroki

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