A DFT mechanistic study of the generation of azomethine ylides from the ring-opening reactions of stabilized aziridines and follow-up 1,3-dipolar cycloaddition reactions with acetaldehyde
Sign Up to like & getrecommendations! Published in 2018 at "Computational and Theoretical Chemistry"
DOI: 10.1016/j.comptc.2018.10.002
Abstract: Abstract This work investigated computationally with density functional theory calculations at the M06/6-311G∗ level, the ring opening reaction of various methyl-, phenyl- and carbonyl- substituted aziridines to obtain azomethine ylides and the subsequent 1,3-dipolar cycloaddition… read more here.
Keywords: kcal mol; ring opening; dipolar cycloaddition; azomethine ylides ... See more keywords
Synthesis of biologically active natural products by [3 + 2] cycloaddition of non-stabilized azomethine ylides (AMY): Concepts and realizations
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2017.01.036
Abstract: Non-stabilized azomethine ylides (AMY) which are represented as a zwitterionic form of a CNC unit having four electrons in three parallel atomic π orbitals perpendicular to the plane of the dipole, undergoes 1,3-dipolar cycloaddition to… read more here.
Keywords: non stabilized; cycloaddition; ylides amy; azomethine ylides ... See more keywords
CuII-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with a chiral ferrocene-derived P,N-ligand
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2017.05.044
Abstract: A ferrocene-derived P,N-heterodonor ligand was effectively used in a Cu(OAc)2·H2O-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with maleate derivatives, affording cycloadducts with high yields (up to 96%), diastereoselectivities (>99 dr), and enantioselectivities (up to 99%… read more here.
Keywords: asymmetric dipolar; azomethine ylides; catalysed asymmetric; ferrocene derived ... See more keywords
Nonstabilized azomethine ylides in the synthesis of aryl cucurbitine derivatives
Sign Up to like & getrecommendations! Published in 2019 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2019.01.047
Abstract: Abstract Nonstabilized azomethine ylides react with 4-arylidene-2-phenyloxazol-5(4H)-ones to form diazaspiro[4.4]nonenes, which were hydrolyzed to aryl cucurbitine derivatives in 35–67% overall yield. read more here.
Keywords: ylides synthesis; aryl cucurbitine; azomethine ylides; nonstabilized azomethine ... See more keywords
Synthesis of spiropyrrolidine oxindoles via Ag-catalyzed stereo- and regioselective 1,3-dipolar cycloaddition of indole-based azomethine ylides with chalcones
Sign Up to like & getrecommendations! Published in 2018 at "New Journal of Chemistry"
DOI: 10.1039/c8nj04492a
Abstract: The synthesis of novel spiropyrrolidine oxindole derivatives was reported, using Ag-catalyzed [3+2] cycloaddition of azomethine ylides generated in situ from the condensation of substituted isatins and primary α-amino acid esters with chalcones. Products bearing four… read more here.
Keywords: cycloaddition; azomethine ylides; synthesis spiropyrrolidine; spiropyrrolidine oxindoles ... See more keywords
Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
Sign Up to like & getrecommendations! Published in 2022 at "Chemical Science"
DOI: 10.1039/d1sc04595d
Abstract: Chiral pyrrolidinyl units are important building blocks in biologically active natural products and drugs, and the development of efficient methods for the synthesis of diverse structured pyrrolidine derivatives is of great importance. Meanwhile, incorporating fluorine… read more here.
Keywords: azomethine ylides; cycloaddition azomethine; dipolar cycloaddition; synthesis bioactive ... See more keywords
Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc02902b
Abstract: An enantioselective synthesis of polycyclic fluorinated pyrrolidines has been achieved by Cu-catalyzed intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles. The method displays a wide scope and afforded the desired cycloadducts in high yields… read more here.
Keywords: dipolar cycloaddition; intramolecular dipolar; cycloaddition azomethine; ylides fluorinated ... See more keywords
Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
Sign Up to like & getrecommendations! Published in 2023 at "Chemical Science"
DOI: 10.1039/d3sc00435j
Abstract: A series of benzofulvenes without any electron-withdrawing substituents were employed as 2π-type dipolarophiles for the first time to participate in Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition (1,3-DC) reactions of azomethine ylides. An intrinsic non-benzenoid aromatic characteristic from… read more here.
Keywords: dipolar cycloaddition; asymmetric dipolar; catalyzed asymmetric; azomethine ylides ... See more keywords
Reactions of 4-Pyrones with Azomethine Ylides as a Chemoselective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines
Sign Up to like & getrecommendations! Published in 2021 at "Synthesis"
DOI: 10.1055/s-0040-1706032
Abstract: 4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double… read more here.
Keywords: pyrano pyrrolidines; azomethine ylides; pyrones azomethine; ylides chemo ... See more keywords
Diastereoselective synthesis of diverse 3,2′-pyrrolidinyl bispirooxindoles via 1,3-dipolar cycloaddition reactions of azomethine ylides with exocyclic α,β-unsaturated ketones and in silico studies for prediction of bioactivity
Sign Up to like & getrecommendations! Published in 2019 at "Synthetic Communications"
DOI: 10.1080/00397911.2018.1560472
Abstract: Abstract A three-component highly regio- and diastereoselective 1,3-dipolar cycloaddition reaction between isatin, a series of primary amino acids (10 nos), and exocyclic α,β-unsaturated ketones was developed towards the synthesis of a small library of bispirooxindole… read more here.
Keywords: azomethine ylides; unsaturated ketones; exocyclic unsaturated; dipolar cycloaddition ... See more keywords
[3+2]-Cycloaddition of azomethine ylides to 5-methylidene-3-aryl-2-сhalcogen-imidazolones: access to dispiro indolinone-pyrrolidine-imidazolones
Sign Up to like & getrecommendations! Published in 2022 at "Royal Society Open Science"
DOI: 10.1098/rsos.211967
Abstract: A synthesis of dispiro derivatives from 5-methylidene-2-chalcogenimidazolones and azomethine ylides generated from isatins and N-substituted α-amino acids has been developed. read more here.
Keywords: ylides methylidene; cycloaddition azomethine; methylidene aryl; halcogen imidazolones ... See more keywords