Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions

The key factors for carbonyl‐stabilised ammonium ylide‐mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the...

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Autores principales: Novacek, Johanna, Roiser, Lukas, Zielke, Katharina, Robiette, Raphaël, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5066843/
https://www.ncbi.nlm.nih.gov/pubmed/27381752
http://dx.doi.org/10.1002/chem.201602052
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author Novacek, Johanna
Roiser, Lukas
Zielke, Katharina
Robiette, Raphaël
Waser, Mario
author_facet Novacek, Johanna
Roiser, Lukas
Zielke, Katharina
Robiette, Raphaël
Waser, Mario
author_sort Novacek, Johanna
collection PubMed
description The key factors for carbonyl‐stabilised ammonium ylide‐mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine‐based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.
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spelling pubmed-50668432016-10-17 Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions Novacek, Johanna Roiser, Lukas Zielke, Katharina Robiette, Raphaël Waser, Mario Chemistry Full Papers The key factors for carbonyl‐stabilised ammonium ylide‐mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine‐based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions. John Wiley and Sons Inc. 2016-07-06 2016-08-01 /pmc/articles/PMC5066843/ /pubmed/27381752 http://dx.doi.org/10.1002/chem.201602052 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Novacek, Johanna
Roiser, Lukas
Zielke, Katharina
Robiette, Raphaël
Waser, Mario
Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions
title Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions
title_full Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions
title_fullStr Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions
title_full_unstemmed Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions
title_short Towards a General Understanding of Carbonyl‐Stabilised Ammonium Ylide‐Mediated Epoxidation Reactions
title_sort towards a general understanding of carbonyl‐stabilised ammonium ylide‐mediated epoxidation reactions
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5066843/
https://www.ncbi.nlm.nih.gov/pubmed/27381752
http://dx.doi.org/10.1002/chem.201602052
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