Azomethine ylides thus have high utility in total synthesis, and formation of chiral ligands and pharmaceuticals. (wikipedia.org)
However, there are only a few examples of such eye lo add it ions being successfully performed with an unstabilised azomethine ylide that has been tethered to a removable chiral auxiliary. (ucl.ac.uk)
In the first part of this thesis, the potential utility of optically pure 1,1-dialkylhydrazines as chiral auxiliaries for nonstabilised azomethine ylide cycloadditions to alkenes has been investigated. (ucl.ac.uk)
While the preparation of several chiral 1,1-dialkylhydrazines was carried out successfully, the formation of the N-amino azomethine ylide precursors from these hydrazines failed, occasionally giving interesting unwanted and unexpected by-products. (ucl.ac.uk)
The second part of this thesis focuses on the evaluation of several new chiral auxiliaries as stereochemical control elements for 1,3-dipolar cycloadditions of azomethine ylides to alkenes. (ucl.ac.uk)
P . An MEDT study of the carbenoid-type [3+2] cycloaddition reactions of nitrile ylides with electron-deficient chiral oxazolidinones. (luisrdomingo.com)
Synthesis3
Dive into the research topics of 'Azomethine Ylide Cycloaddition Approach toward Dendrobine: Synthesis of 5-Deoxymubironine C'. Together they form a unique fingerprint. (nyu.edu)
Azomethine Ylide Cycloaddition Approach toward Dendrobine: Synthesis of 5-Deoxymubironine C . Journal of Organic Chemistry , 83 (6), 3061-3068. (nyu.edu)
His doctoral research concerned the generation of nonstabilized azomethine ylides using desilylation methods its application to the synthesis of pyrrolizidine alkaloids (publications 2-3). (cleancompetition.org)
Cycloaddition reactions8
Three different ylide shapes are possible, each leading to different stereochemistry in the products of 1,3-dipolar cycloaddition reactions. (wikipedia.org)
As with other cycloaddition reactions of a 1,3-dipole with a π-system, 1,3-dipolar cycloaddition using an azomethine ylide is a six-electron process. (wikipedia.org)
In these reactions, the azomethine ylide is typically the HOMO, and the electron-deficient dipolarophile the LUMO, although cycloaddition reactions with unactivated π-systems are known to occur, especially when the cyclization is intramolecular. (wikipedia.org)
1,3-Dipolar cycloaddition reactions of azomethine ylides commonly use alkenes or alkynes as dipolarophiles, to form pyrrolidines or pyrrolines, respectively. (wikipedia.org)
P. A Molecular Electron Density Theory Study of the Role of the Copper-Metallation of Azomethine Ylides in [3+2] Cycloaddition Reactions. (luisrdomingo.com)
Ríos-Gutiérrez, M . A. Molecular Electron Density Theory Study of the Reactivity of Azomethine Imine in [3+2] Cycloaddition Reactions. (luisrdomingo.com)
P. A new model for C-C bond formation processes derived from the Molecular Electron-Density Theory in the study of the mechanism of [3+2] cycloaddition reactions of carbenoid nitrile ylides with electron-deficient ethylenes. (luisrdomingo.com)
This spiro-fused adducts are readily available via one-pot three-component 1,3-dipolar cycloaddition reactions of cyclopropenes and azomethine ylides (generated in situ from amino acids and oxindoles). (sciforum.net)
Iodonium Ylides1
Protasiewicz, J. D., "Solid State Aggregation of Cyclic Iodonium Ylides" Arkivoc (invited, special issue on Hypervalent Iodine - ICHIC Moscow Conference) 2021 . (case.edu)
Derivatives1
A novel series of dispiro(indolinonepyrrolidineiminothiazolidinones) were synthesized by 1,3-dipolar cycloaddition of 5-arylmethylidene-2-iminothiazolidin-4-ones and azomethine ylides generated from N -alkylamino acids and isatin derivatives. (osi.lv)
Alkenes1
The [3+2]-cycloaddition reaction of nonstabilised azomethine ylides to alkenes is a valuable synthetic method for the assembly of functionalised pyrrolidines. (ucl.ac.uk)
Imines1
Another way to form azomethine ylides from imines is by prototropy and by alkylation. (wikipedia.org)
Polycyclic2
Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling. (mpg.de)
Initially, his program focused on the use of pyran-4-one photochemistry for the rapid assembly of complex polycyclic skeletons, and the Stevens rearrangement of metallocarbene-derived ylides. (cleancompetition.org)
Methods1
One of the easiest methods of forming azomethine ylides is by condensation of an aldehyde with an amine. (wikipedia.org)
Generated in situ1
β-Nitrostyrenes were used as dipolarophiles, while the 1,3-dipole component was the azomemthine ylide, generated in situ from indenoquinoxaline and l-phenylalanine. (nih.gov)
Enantioselective1
Novel ferrocenyl substituted aziridinyl methanol (FAM) ligands were synthesized and successfully used in metal-promoted catalytic enantioselective azomethine ylide cycloadditions, diethylzinc additions to enones, alkynylzinc additions to aldehydes, diethylzinc additions to aldehydes, and Henry reactions. (metu.edu.tr)
Derivatives2
12. Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidines. (nih.gov)
reported the formation of some spirooxindole derivatives 44 and 45 through a three-component 1,3-dipolar cycloaddition of the azomethine ylide produced in situ from sarcosine (41a) or L-proline (41b) and isatin 42 using the dipolarophile 1,4-naphthoquinone 43 accompanied by spontaneous surroundings oxidation in atmospheric reflux circumstances (System 17) [59]. (engineering-gdfsuez.com)