Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines

The electrochemical generation of menthylamines from the corresponding menthone oximes equipped with an additional substituent in position 8 is described. Due to 1,3-diaxial interactions a pronounced diastereoselectivity for the menthylamines is found.

Detalles Bibliográficos
Autores principales: Edinger, Carolin, Kulisch, Jörn, Waldvogel, Siegfried R
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362023/
https://www.ncbi.nlm.nih.gov/pubmed/25815083
http://dx.doi.org/10.3762/bjoc.11.34
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author Edinger, Carolin
Kulisch, Jörn
Waldvogel, Siegfried R
author_facet Edinger, Carolin
Kulisch, Jörn
Waldvogel, Siegfried R
author_sort Edinger, Carolin
collection PubMed
description The electrochemical generation of menthylamines from the corresponding menthone oximes equipped with an additional substituent in position 8 is described. Due to 1,3-diaxial interactions a pronounced diastereoselectivity for the menthylamines is found.
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spelling pubmed-43620232015-03-26 Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines Edinger, Carolin Kulisch, Jörn Waldvogel, Siegfried R Beilstein J Org Chem Full Research Paper The electrochemical generation of menthylamines from the corresponding menthone oximes equipped with an additional substituent in position 8 is described. Due to 1,3-diaxial interactions a pronounced diastereoselectivity for the menthylamines is found. Beilstein-Institut 2015-02-27 /pmc/articles/PMC4362023/ /pubmed/25815083 http://dx.doi.org/10.3762/bjoc.11.34 Text en Copyright © 2015, Edinger et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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 Full Research Paper
Edinger, Carolin
Kulisch, Jörn
Waldvogel, Siegfried R
Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
title Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
title_full Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
title_fullStr Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
title_full_unstemmed Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
title_short Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines
title_sort stereoselective cathodic synthesis of 8-substituted (1r,3r,4s)-menthylamines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362023/
https://www.ncbi.nlm.nih.gov/pubmed/25815083
http://dx.doi.org/10.3762/bjoc.11.34
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AT kulischjorn stereoselectivecathodicsynthesisof8substituted1r3r4smenthylamines
AT waldvogelsiegfriedr stereoselectivecathodicsynthesisof8substituted1r3r4smenthylamines

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