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First application of fluorinated nitrones for the synthesis of fluoroalkylated β-lactams via the Kinugasa reaction


Kowalski, Marcin K; Mloston, Grzegorz; Obijalska, Emilia; Linden, Anthony; Heimgartner, Heinz (2016). First application of fluorinated nitrones for the synthesis of fluoroalkylated β-lactams via the Kinugasa reaction. Tetrahedron, 72(35):5305-5313.

Abstract

The regioselective reactions of fluorinated nitrones with selected terminal alkynes (Kinugasa reaction) was studied in the presence of Cu(I) iodide and TEA as a base. After chromatographic purification the desired β-lactams were obtained in high yields (up to 93%) and high diastereoselectivities (up to 9:1). The reactions performed in the presence of chiral, enantiomerically pure ligands led to enantiomerically enriched products (ee values up to 26%) obtained as one of the possible diastereoisomers depending on the type of chiral ligand used.

Abstract

The regioselective reactions of fluorinated nitrones with selected terminal alkynes (Kinugasa reaction) was studied in the presence of Cu(I) iodide and TEA as a base. After chromatographic purification the desired β-lactams were obtained in high yields (up to 93%) and high diastereoselectivities (up to 9:1). The reactions performed in the presence of chiral, enantiomerically pure ligands led to enantiomerically enriched products (ee values up to 26%) obtained as one of the possible diastereoisomers depending on the type of chiral ligand used.

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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:2016
Deposited On:05 Aug 2016 09:06
Last Modified:08 Dec 2017 20:07
Publisher:Elsevier
ISSN:0040-4020
Funders:National Science Center (PL-Cracow) (Grant OPUS–7 (UMO–2014/13/B/ST5/04004))
Publisher DOI:https://doi.org/10.1016/j.tet.2016.06.073

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