4-Isoxazolines and pyrroles from allenoates

Lopes, Susana M. M.; Nunes, Cláudio M.; Melo, Teresa M. V. D. Pinho e

doi:10.1016/j.tet.2010.06.010

Cited by 28 publications

(2 citation statements)

References 33 publications

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“…3 The incorporation of these groups benefits the transformation not only by inducing regioselectivity but also by introducing extra handles for product derivation and decreasing activation energy. Several catalyst-free 1,3-dipolar cycloadditions [28][29][30][31][32][33][34][35][36] for the synthesis of 4-isoxazolines have been reported, and most of them required elevated reaction temperatures in organic solvents, cyclic nitrones or alkynes activated by two electron-withdrawing groups. Sulfoxides play a pivotal role in chemistry and biology.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of (polyfluoro)alkanesulfinyl 4-isoxazolines: a stepwise solvent- and catalyst-free approach or a one-pot process in water

Liao

Gao

et al. 2023

Green Chem.

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Section: Introductionmentioning

confidence: 99%

Facile synthesis of (polyfluoro)alkanesulfinyl 4-isoxazolines: a stepwise solvent- and catalyst-free approach or a one-pot process in water

Liao

Gao

et al. 2023

Green Chem.

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“…Interestingly, when this cycloaddition was run at higher temperatures, or when 18 was isolated, redissolved in toluene, and heated, pyrrole 19 was formed, albeit in extremely low yields (≤12%). Formation of pyrroles from dipolarophilic alkynes and nitrones derived from ketones, under heating, is precedented . Additionally, and also under unoptimized conditions, nitrone 10g was converted to ketone 20 in 63% yield .…”

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confidence: 99%

Dienamine-Catalyzed Nitrone Formation via Redox Reaction

Fraboni

Brenner‐Moyer

2016

Org. Lett.

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The first catalytic method to directly introduce nitrone functionality onto aldehyde substrates is described. This reaction proceeds by an unprecedented organocatalytic redox mechanism in which an enal is oxidized to the γ-nitrone via dienamine catalysis, thereby reducing an equivalent of nitrosobenzene. This reaction is a unique example of divergent reactivity of an enal, which represents a novel strategy for rapidly accessing small libraries of N,O-heterocycles. Alternatively, divergent reactivity can be suppressed simply by changing solvents.

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Enantioselective Synthesis of 4‐Isoxazolines by 1,3‐Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines

et al. 2012

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The first organocatalytic enantioselective 1,3‐dipolar reaction between nitrones and alkynals catalyzed by (S)‐2‐(fluorodiphenylmethyl)pyrrolidine to give 4‐isoxazolines (2,3‐dihydroisoxazoles) with high enantiomeric excess, excellent yields and low catalyst loading (1–5 mol%) is presented. The catalytic loading could be reduced to 1 mol% with only slight increases in reaction times.

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4-Isoxazolines and pyrroles from allenoates

Cited by 28 publications

References 33 publications

Facile synthesis of (polyfluoro)alkanesulfinyl 4-isoxazolines: a stepwise solvent- and catalyst-free approach or a one-pot process in water

Facile synthesis of (polyfluoro)alkanesulfinyl 4-isoxazolines: a stepwise solvent- and catalyst-free approach or a one-pot process in water

Dienamine-Catalyzed Nitrone Formation via Redox Reaction

Enantioselective Synthesis of 4‐Isoxazolines by 1,3‐Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines

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