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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

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

A straightforward synthesis of a new family of molecules: 2,5,8-trialkoxyheptazines. Application to photoredox catalyzed transformations

We have prepared several 2,5,8-trialkoxyheptazines starting from the soluble precursor 2,5,8-tris(3,5-diethylpyrazolyl)-heptazine. We present their synthesis along with their promising spectroscopic and electrochemical properties, which demonstrate large

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route t

Zinc mediated direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones and mechanistic insight

A Lewis acid catalyzed direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones in the presence of aqueous Zn(II)-salts has been described. This investigation also provides a novel observation for the stoichiometric role of Zn-halides over what is known to date for catalytic processes. A thorough mechanistic study has been established based on the experiment using18O-labeled water in optimized reaction conditions; the incorporation of18O in the desired product was also substantiated by HRMS. This methodology is also a mild, inexpensive, and an efficient approach for this unusual conversion.

REGULATORS FOR CONTROLLING LINEAR AND PSEUDO-RING EXPANSION POLYMERIZATION OF VINYL MONOMERS

The invention concerns new regulator compounds for a novel polymerization process for vinyl monomers, which yields polymers with improved control over composition and nearly full to full conservation of architectural integrity up to high conversion. The regulator compounds are defined by according to anyone of the Formulas (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H) and (1I), wherein R1 stands for an optionally substituted secondary or tertiary alkyl or secondary or tertiary aralkyl; Z1 stands for -CN or a carboxylic acid ester of formula C(O)OR21; Z2 may be chosen from the group of -CN, carboxylic acid, salts of carboxylic acids, carboxylic acid ester, carboxylic acid amides, (hetero)aryl, alkenyl and halogen; R2, R3, R4 and R5 are each independently chosen from the group of H, alkyl, aralkyl, (hetero)aryl, -CN and carboxylic acid ester of formula C(O)OR22; R7 stands for a primary alkyl or primary aralkyl, -CN or hydrogen; Y stands for a bridging group and n is 2, 3, 4, 5 or 6; in case R1 stands for tertiary alkyl or tertiary aralkyl, R6 stands for a primary alkyl or primary aralkyl, -CN or a carboxylic acid ester of formula C(O)OR26; in case R1 stands for a secondary alkyl or secondary aralkyl, R6 stands for a primary or secondary alkyl or primary or secondary aralkyl, -CN, a carboxylic acid ester of formula C(O)OR26 or a phosphonic acid ester of formula P(O)(OR27)2, a (hetero)aryl or an alkenyl; R21, R22, R26 and R27 each independently stand for alkyl or aralkyi having from 1-30 carbon atoms, optionally containing heteroatoms.

Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.

Organotin-oxotungstate coordination polymer: An efficient catalyst for the selective oxidation of amines

The organometallic coordination polymer [(nBu3Sn)2WO4] catalyzed the selective oxidation of secondary and primary amines to nitrones and oximes, respectively. The catalyst was found to be reusable for five catalytic cycles without any appreciable loss in activity. Under the optimized reaction conditions [4 mol% catalyst, 3-4 equiv of hydrogen peroxide (30 wt%, aqueous solution), methanol as the solvent, r.t.], the corresponding nitrones and oximes were obtained with good efficiency.

Oxidation of secondary amines to nitrones using magnetically separable tungstophosphoric acid supported on silica-encapsulated γ-Fe 2O3 nanoparticles

Superparamagnetic tungstophosphoric acid supported on silica-encapsulated γ-Fe2O3 was used as an efficient catalyst for the direct oxidation of secondary amines to nitrones with hydrogen peroxide as the oxidant. The catalyst could be recycled up to four times without significant loss of activity.

An efficient ecofriendly protocol for the synthesis of novel fluoro isoxazoline and isoxazolidines using N-benzyl fluoro nitrone via cycloaddition reactions

1-Butyl-3-methylimidazolium based ionic liquids are found to accelerate significantly the intermolecular 1,3-dipolar cycloaddition of N-benzyl fluoro nitrones derived in situ from aldehydes and benzylhydroxylamine, with electron deficient alkynes to affor