Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage

The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C–F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditions to yield the corresponding α-hydroxyacetal...

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Autores principales: Shibatomi, Kazutaka, Kitahara, Kazumasa, Okimi, Takuya, Abe, Yoshiyuki, Iwasa, Seiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5975931/
https://www.ncbi.nlm.nih.gov/pubmed/29910896
http://dx.doi.org/10.1039/c5sc03486h
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author Shibatomi, Kazutaka
Kitahara, Kazumasa
Okimi, Takuya
Abe, Yoshiyuki
Iwasa, Seiji
author_facet Shibatomi, Kazutaka
Kitahara, Kazumasa
Okimi, Takuya
Abe, Yoshiyuki
Iwasa, Seiji
author_sort Shibatomi, Kazutaka
collection PubMed
description The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C–F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditions to yield the corresponding α-hydroxyacetals in a stereospecific manner. Accordingly, the one-pot conversion of α-branched aldehydes into α-hydroxyacetals was achieved for the first time in high enantioselectivity.
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spelling pubmed-59759312018-06-15 Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage Shibatomi, Kazutaka Kitahara, Kazumasa Okimi, Takuya Abe, Yoshiyuki Iwasa, Seiji Chem Sci Chemistry The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C–F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditions to yield the corresponding α-hydroxyacetals in a stereospecific manner. Accordingly, the one-pot conversion of α-branched aldehydes into α-hydroxyacetals was achieved for the first time in high enantioselectivity. Royal Society of Chemistry 2016-02-01 2015-11-16 /pmc/articles/PMC5975931/ /pubmed/29910896 http://dx.doi.org/10.1039/c5sc03486h Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Shibatomi, Kazutaka
Kitahara, Kazumasa
Okimi, Takuya
Abe, Yoshiyuki
Iwasa, Seiji
Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
title Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
title_full Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
title_fullStr Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
title_full_unstemmed Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
title_short Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage
title_sort enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific c–f bond cleavage
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5975931/
https://www.ncbi.nlm.nih.gov/pubmed/29910896
http://dx.doi.org/10.1039/c5sc03486h
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