Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines

A conceptually novel, high‐yielding, mono‐ or bis‐homologation was realized with lithium halocarbenoids and enables the one‐step, fully chemocontrolled assembly of a new class of quaternary trifluoromethyl aziridines. Trifluoroacetimidoyl chlorides (TFAICs) act as convenient electrophilic platforms,...

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Autores principales: Ielo, Laura, Touqeer, Saad, Roller, Alexander, Langer, Thierry, Holzer, Wolfgang, Pace, Vittorio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6582437/
https://www.ncbi.nlm.nih.gov/pubmed/30548145
http://dx.doi.org/10.1002/anie.201812525
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author Ielo, Laura
Touqeer, Saad
Roller, Alexander
Langer, Thierry
Holzer, Wolfgang
Pace, Vittorio
author_facet Ielo, Laura
Touqeer, Saad
Roller, Alexander
Langer, Thierry
Holzer, Wolfgang
Pace, Vittorio
author_sort Ielo, Laura
collection PubMed
description A conceptually novel, high‐yielding, mono‐ or bis‐homologation was realized with lithium halocarbenoids and enables the one‐step, fully chemocontrolled assembly of a new class of quaternary trifluoromethyl aziridines. Trifluoroacetimidoyl chlorides (TFAICs) act as convenient electrophilic platforms, enabling the addition of either one or two homologating elements by simply controlling the stoichiometry of the process. Mechanistic studies highlighted that the homologation event, carried out with two different carbenoids (LiCH(2)Cl and LiCH(2)F), leads to fluoromethyl analogues in which the first nucleophile is employed for constructing the cycle and the second for decorating the resulting molecular architecture.
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spelling pubmed-65824372019-06-24 Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines Ielo, Laura Touqeer, Saad Roller, Alexander Langer, Thierry Holzer, Wolfgang Pace, Vittorio Angew Chem Int Ed Engl Communications A conceptually novel, high‐yielding, mono‐ or bis‐homologation was realized with lithium halocarbenoids and enables the one‐step, fully chemocontrolled assembly of a new class of quaternary trifluoromethyl aziridines. Trifluoroacetimidoyl chlorides (TFAICs) act as convenient electrophilic platforms, enabling the addition of either one or two homologating elements by simply controlling the stoichiometry of the process. Mechanistic studies highlighted that the homologation event, carried out with two different carbenoids (LiCH(2)Cl and LiCH(2)F), leads to fluoromethyl analogues in which the first nucleophile is employed for constructing the cycle and the second for decorating the resulting molecular architecture. John Wiley and Sons Inc. 2019-01-24 2019-02-18 /pmc/articles/PMC6582437/ /pubmed/30548145 http://dx.doi.org/10.1002/anie.201812525 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Ielo, Laura
Touqeer, Saad
Roller, Alexander
Langer, Thierry
Holzer, Wolfgang
Pace, Vittorio
Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
title Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
title_full Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
title_fullStr Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
title_full_unstemmed Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
title_short Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
title_sort telescoped, divergent, chemoselective c1 and c1‐c1 homologation of imine surrogates: access to quaternary chloro‐ and halomethyl‐trifluoromethyl aziridines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6582437/
https://www.ncbi.nlm.nih.gov/pubmed/30548145
http://dx.doi.org/10.1002/anie.201812525
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