Practical cleavage of trifluoroacetamides with p-toluensulfonic acid

Spencer, C. C.; Balsells, Jaume; Li, Hongmei

doi:10.1016/j.tetlet.2008.12.050

Cited by 9 publications

(6 citation statements)

References 11 publications

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“…In pursuit of an alternative protocol, we followed Li et al, approach which involves treatment with p-TsOH. 19 This method also facilitates the isolation of product after simple work-up. In the present study (Scheme 3), Ugi products 4 were treated with p-TsOH in MeOH at 50 C, and the final product 5 was formed over 30 min (TLC analysis).…”

Section: Resultsmentioning

confidence: 99%

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Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

et al. 2012

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Enantiopure N b -Fmoc-amino alkyl isonitriles and amino acid esters have been employed as building blocks in Ugi four-component reaction (U-4CR) to yield 1,1 0 -iminodicarboxylated peptidomimetics. By employing trifluoroacetic acid as one of the components, a different outcome has been observed and rationalized. Ugi products are obtained as trifluoroacetamide adducts, which on further reaction under mild acidic conditions lead to the title compounds. The method has also been proven to be useful for the preparation of ethyl, benzyl and tert-butyl esters.

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Section: Resultsmentioning

confidence: 99%

“…1 H NMR and 13 C NMR spectra were recorded on a Bruker AMX 300 MHz and 100 MHz spectrometers, respectively. 19 F NMR was recorded on a Bruker AMX 376 MHz (internal standard CFCl 3 ). Melting points were determined in an open capillary and are uncorrected.…”

Section: Generalmentioning

confidence: 99%

Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

et al. 2012

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“…E-mail: hosseinanaraki@yahoo.com organic chemistry. 12 Because of this widespread use, several methods for the trifluoroacetylation of amines using, for example, trifluoroacetic anhydride, 15 S-ethyl trifluorothioacetate, 13 N-(trifluoroacetyl)imidazole, 14 Continuing our studies on IMCRs, 20-23 we report here the results of our study on the reaction between cyclohexyl isocyanide, aromatic aldehydes, aromatic amines and trifluoroacetic anhydride (TFAA).…”

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confidence: 96%

“…E-mail: hosseinanaraki@yahoo.com organic chemistry. 12 Because of this widespread use, several methods for the trifluoroacetylation of amines using, for example, trifluoroacetic anhydride, 15 S-ethyl trifluorothioacetate, 13 N-(trifluoroacetyl)imidazole, 14 2-[(trifluoroacetyl)oxy] pyridine, 15 trifluoroacetyl triflate, 16 N-(trifluoroacetoxy)succinimi de, 17 (trifluoroacetyl)benzotriazole 18 and N-(trifluoroacetyl) succinimide 19 as trifluoroacetylating reagents have been developed.…”

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confidence: 99%

Four-Component Reaction between Cyclohexyl Isocyanide, Aromatic Aldehydes, Aromatic Amines and Trifluoroacetic Anhydride

Anary‐Abbasinejad

Anaraki‐Ardakani

Rasekh

et al. 2010

Journal of Chemical Research

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Reaction of cyclohexyl isocyanide with aromatic aldehydes, aniline derivatives and trifluoroacetic anhydride in dichloromethane at room temperature afforded N-[cyclohexylcarbamoyl(aryl)methyl]-2,2,2-trifluoro-N-arylacetamide derivatives in nearly quantitative yields after 10 min. The work-up procedure is very easy and the products are precipitated in ether as pure solids. The structure of one of the products was established by X-ray single crystal analysis.

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“…The 2,2,2-trifluoroacetyl group can be removed by hydrolysis under mild conditions. [25] This catalytic asymmetric g-amination process is not limited to additions of 2,2,2-trifluoroacetamide to carbethoxy-substituted allenoates. For example, it can also be applied to reactions with a methyl and a tert-butyl ester, as well as with a Weinreb amide, in ca.…”

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confidence: 99%

Catalytic Asymmetric CN Bond Formation: Phosphine‐Catalyzed Intra‐ and Intermolecular γ‐Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates

et al. 2013

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The first examples are described of catalyzed γ-additions of nitrogen nucleophiles to γ-substituted alkynoates or allenoates that proceed with good efficiency, specifically, intra- and intermolecular processes that employ distinct and useful families of nitrogen nucleophiles (anilines and 2,2,2-trifluoroacetamide), catalyzed by spirophosphine 1. Furthermore, the first demonstrations are reported of asymmetric reactions, affording interesting classes of target molecules such as enantioenriched pyrrolidines, indolines, and γ-amino-α,β-unsaturated carbonyl compounds.

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Practical cleavage of trifluoroacetamides with p-toluensulfonic acid

Cited by 9 publications

References 11 publications

Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

Four-Component Reaction between Cyclohexyl Isocyanide, Aromatic Aldehydes, Aromatic Amines and Trifluoroacetic Anhydride

Catalytic Asymmetric CN Bond Formation: Phosphine‐Catalyzed Intra‐ and Intermolecular γ‐Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates

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