Enantioselective 5-exo-Fluorocyclization of Ene-Oximes

The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry...

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Autores principales: Rouno, Taiki, Niwa, Tomoki, Nishibashi, Kousuke, Yamamoto, Nobuharu, Egami, Hiromichi, Hamashima, Yoshitaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804199/
https://www.ncbi.nlm.nih.gov/pubmed/31554247
http://dx.doi.org/10.3390/molecules24193464
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author Rouno, Taiki
Niwa, Tomoki
Nishibashi, Kousuke
Yamamoto, Nobuharu
Egami, Hiromichi
Hamashima, Yoshitaka
author_facet Rouno, Taiki
Niwa, Tomoki
Nishibashi, Kousuke
Yamamoto, Nobuharu
Egami, Hiromichi
Hamashima, Yoshitaka
author_sort Rouno, Taiki
collection PubMed
description The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be S by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline.
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spelling pubmed-68041992019-11-18 Enantioselective 5-exo-Fluorocyclization of Ene-Oximes Rouno, Taiki Niwa, Tomoki Nishibashi, Kousuke Yamamoto, Nobuharu Egami, Hiromichi Hamashima, Yoshitaka Molecules Communication The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be S by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline. MDPI 2019-09-24 /pmc/articles/PMC6804199/ /pubmed/31554247 http://dx.doi.org/10.3390/molecules24193464 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Rouno, Taiki
Niwa, Tomoki
Nishibashi, Kousuke
Yamamoto, Nobuharu
Egami, Hiromichi
Hamashima, Yoshitaka
Enantioselective 5-exo-Fluorocyclization of Ene-Oximes
title Enantioselective 5-exo-Fluorocyclization of Ene-Oximes
title_full Enantioselective 5-exo-Fluorocyclization of Ene-Oximes
title_fullStr Enantioselective 5-exo-Fluorocyclization of Ene-Oximes
title_full_unstemmed Enantioselective 5-exo-Fluorocyclization of Ene-Oximes
title_short Enantioselective 5-exo-Fluorocyclization of Ene-Oximes
title_sort enantioselective 5-exo-fluorocyclization of ene-oximes
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804199/
https://www.ncbi.nlm.nih.gov/pubmed/31554247
http://dx.doi.org/10.3390/molecules24193464
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