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Relevant academic research and scientific papers

Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones

An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is

Accessing benzooxadiazepines: Via formal [4 + 3] cycloadditions of aza- o -quinone methides with nitrones

An unprecedented and efficient [4 + 3] cycloaddition of N-(ortho-chloromethyl)aryl amides with nitrones has been developed. This approach provides easy access to a series of seven-membered benzooxadiazepine derivatives in good to excellent yields (up to 99% yield) under mild reaction conditions.

A highly diastereoselective [3+3] annulation reaction of aza-oxyallyl cations and nitrones

An efficient synthesis of 1,2,4-oxadiazinan-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallyl cations with nitrones has been developed. The protocol features easy operation, excellent yields, excellent diastereo-control, broad substrate sco

α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric exo-Selective 1,3-Dipolar Cycloaddition with Nitrones

1,3-Dipolar cycloaddition is a commonly exploited method to access 5-membered chemical entities with a variety of peripheral functionalities and their stereochemical arrangements. Nitrones are isolable 1,3-dipoles that exhibit sufficient reactivity toward electron-deficient olefins in the presence of Lewis acids to deliver highly substituted isoxazolidines. Herein we document that α,β-unsaturated amides, generally regarded as barely reactive in a 1,3-dipolar reaction manifold, were effectively activated using the designed 7-azaindoline auxiliary in an In(OTf)3/bishydroxamic acid catalytic system. The broad substrate scope and clean removal of the 7-azaindoline auxiliary from the product highlight the synthetic utility of the present catalysis.

A magnetoclick imidazolidinone nanocatalyst for asymmetric 1,3-dipolar cycloadditions

A 1,3-dipolar azide-alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3-dipolar cycloaddition between nitrones and α,β-unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo- and enantioselectivities of the isoxazolidines. Copyright

Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes

Strain-promoted cycloadditions of nitrones with cyclooctynes (k2 = 1.5 M-1 s-1 at 25 °C) are up to 25 times more rapid than comparable reactions of azides. The Royal Society of Chemistry 2010.

Indium (Zinc)-copper-mediated barbier-type alkylation reaction of nitrones in water: Synthesis of amines and hydroxylamines

An efficient method for the Barbier-type alkylation reaction of various nitrones (including chiral version) and alkyl halides in water is described. The amines and hydroxylamines can be obtained in good yields, depending on the judicious choice of the metal complexes used.

Solvent-free synthesis of nitrones in a ball-mill

Various C-aryl and C-alkyl-nitrones were synthesized within 0.5-2 h via condensation of an equimolar amount of aldehydes and N-substituted-hydroxylamines under solvent-free conditions in?a ball-mill apparatus. Reactions can be performed without the need of excluding air and moisture and yields the expected products with no need for further purification. The study has been complemented by Differential Scanning Calorimetry (DSC) and solid-state 13C MAS nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed the superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone (2-PyBN).

Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral Lewis acid

A μ-oxo-type chiral bis-Ti(IV) oxide (S,S)-1 can be successfully utilized in the asymmetric 1,3-dipolar cycloaddition reactions between various nitrones 2 and acrolein to give the corresponding isoxazolidines with high to excellent enantioselectivities. F

Regio- and stereoselectivity of captodative olefins in 1,3-dipolar cycloadditions. A DFT/HSAB theory rationale for the observed regiochemistry of nitrones

Captodative olefins 1-acetylvinyl carboxylates proved to be highly regioselective dipolarophiles in 1,3-dipolar cycloadditon to propionitrile oxide, arylphenylnitrile imines, diazoalkanes, and nitrones to yield the corresponding 5-substituted heterocycles