Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis

A reagent-controlled enantioselectivity switch was uncovered in the asymmetric α-fluorination of β-ketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantios...

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Detalles Bibliográficos
Autores principales: You, Yang'en, Zhang, Long, Luo, Sanzhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5358536/
https://www.ncbi.nlm.nih.gov/pubmed/28451209
http://dx.doi.org/10.1039/c6sc03109a
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author You, Yang'en
Zhang, Long
Luo, Sanzhong
author_facet You, Yang'en
Zhang, Long
Luo, Sanzhong
author_sort You, Yang'en
collection PubMed
description A reagent-controlled enantioselectivity switch was uncovered in the asymmetric α-fluorination of β-ketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantioselectivity. Mechanistic studies disclosed dual H-bonding and electrostatic stereocontrolling modes for the catalysis.
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spelling pubmed-53585362017-04-27 Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis You, Yang'en Zhang, Long Luo, Sanzhong Chem Sci Chemistry A reagent-controlled enantioselectivity switch was uncovered in the asymmetric α-fluorination of β-ketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantioselectivity. Mechanistic studies disclosed dual H-bonding and electrostatic stereocontrolling modes for the catalysis. Royal Society of Chemistry 2017-01-01 2016-08-26 /pmc/articles/PMC5358536/ /pubmed/28451209 http://dx.doi.org/10.1039/c6sc03109a Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
You, Yang'en
Zhang, Long
Luo, Sanzhong
Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
title Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
title_full Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
title_fullStr Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
title_full_unstemmed Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
title_short Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
title_sort reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5358536/
https://www.ncbi.nlm.nih.gov/pubmed/28451209
http://dx.doi.org/10.1039/c6sc03109a
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AT luosanzhong reagentcontrolledenantioselectivityswitchfortheasymmetricfluorinationofbketocarbonylsbychiralprimaryaminecatalysis

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