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Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols


Mloston, Grzegorz; Obijalska, Emilia; Ziebacz, Paulia; Matyszewski, Krzysztof; Urbaniak, Katarzyna; Linden, Anthony; Heimgartner, Heinz (2013). Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols. Journal of Fluorine Chemistry, 156:192-197.

Abstract

A convenient synthesis of alpha-(aziridin-2-yl)-alpha-(trifluoromethyl) alcohols starting with ethyl aziridine-2-carboxylates is reported. Grignard reaction with the corresponding Weinreb amides led to aziridin-2-yl ketones, and subsequent treatment with Ruppert-Prakash reagent gave the trimethylsilylated target compounds as mixtures of diastereoisomers, which were desilylated with TBAF. In the case of ethyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate, (S,S)- and (S,R)-aziridin-2-yl ketones were obtained, separated chromatographically and transformed into the desired enantiomerically pure alpha-trifluoromethylated alcohols.

Abstract

A convenient synthesis of alpha-(aziridin-2-yl)-alpha-(trifluoromethyl) alcohols starting with ethyl aziridine-2-carboxylates is reported. Grignard reaction with the corresponding Weinreb amides led to aziridin-2-yl ketones, and subsequent treatment with Ruppert-Prakash reagent gave the trimethylsilylated target compounds as mixtures of diastereoisomers, which were desilylated with TBAF. In the case of ethyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate, (S,S)- and (S,R)-aziridin-2-yl ketones were obtained, separated chromatographically and transformed into the desired enantiomerically pure alpha-trifluoromethylated alcohols.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:December 2013
Deposited On:07 Nov 2013 15:06
Last Modified:21 Nov 2017 16:54
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center, Poland
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2013.09.011

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