How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones

[Image: see text] The origin of selectivity in the α-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining...

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Autores principales: Lam, Yu-hong, Houk, K. N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4105079/
https://www.ncbi.nlm.nih.gov/pubmed/24967514
http://dx.doi.org/10.1021/ja504714m
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author Lam, Yu-hong
Houk, K. N.
author_facet Lam, Yu-hong
Houk, K. N.
author_sort Lam, Yu-hong
collection PubMed
description [Image: see text] The origin of selectivity in the α-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining the sense and level of enantiofacial selectivity.
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spelling pubmed-41050792015-06-26 How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones Lam, Yu-hong Houk, K. N. J Am Chem Soc [Image: see text] The origin of selectivity in the α-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining the sense and level of enantiofacial selectivity. American Chemical Society 2014-06-26 2014-07-09 /pmc/articles/PMC4105079/ /pubmed/24967514 http://dx.doi.org/10.1021/ja504714m Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Lam, Yu-hong
Houk, K. N.
How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
title How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
title_full How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
title_fullStr How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
title_full_unstemmed How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
title_short How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones
title_sort how cinchona alkaloid-derived primary amines control asymmetric electrophilic fluorination of cyclic ketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4105079/
https://www.ncbi.nlm.nih.gov/pubmed/24967514
http://dx.doi.org/10.1021/ja504714m
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