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...

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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
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author Mitsudo, Koichi
Yamamoto, Junya
Akagi, Tomoya
Yamashita, Atsuhiro
Haisa, Masahiro
Yoshioka, Kazuki
Mandai, Hiroki
Ueoka, Koji
Hempel, Christian
Yoshida, Jun-ichi
Suga, Seiji
author_facet Mitsudo, Koichi
Yamamoto, Junya
Akagi, Tomoya
Yamashita, Atsuhiro
Haisa, Masahiro
Yoshioka, Kazuki
Mandai, Hiroki
Ueoka, Koji
Hempel, Christian
Yoshida, Jun-ichi
Suga, Seiji
author_sort Mitsudo, Koichi
collection PubMed
description 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.
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spelling pubmed-60091802018-07-05 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 Beilstein J Org Chem Letter 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. Beilstein-Institut 2018-05-24 /pmc/articles/PMC6009180/ /pubmed/29977386 http://dx.doi.org/10.3762/bjoc.14.100 Text en Copyright © 2018, Mitsudo et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
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
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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Letter
url 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
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