113273-75-9Relevant academic research and scientific papers
1,3-Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst
Lledó, David,Grindlay, Guillermo,Sansano, José Miguel
, p. 4095 - 4100 (2019/06/25)
The synthesis of a task-specific ionic liquid (TSIL) based on a BMIM ionic liquid phosphane is achieved by modification of the original procedure. It is used as a ligand with AgOAc, and the resulting complex is fully characterized. This catalytic system promotes the 1,3-dipolar cycloaddition of stabilized azomethine ylides and electrophilic alkenes using a green methodology. The green character was analyzed using an overall set of parameters finding the optimal conditions and individualized separation/purification methods for each cycloadduct. The determination of the most important green metrics is reported in this survey, demonstrating the value of this methodology on a laboratory scale or even at an industrial level.
1,3-dipolar cycloaddition of schriff bases and electron-deficient alkenes, catalyzed by α-Amino acids
Kudryavtsev,Zagulyaeva
, p. 378 - 387 (2008/12/22)
L-α-Amino acids catalyze 1,3-dipolar cycloaddition of methyl α-benzylideneamino acids to electron-deficient olefins in different solvents at room temperature. L-α-Amino acids ensure stereoselective formation of the corresponding syn,syn-azomethine ylides. The subsequent reaction with an active dipolarophile is stereospecific; it occurs as endo-cycloaddition with low asymmetric induction (up to ee 12%.). 3,4-Substituted 5-arylprolines were obtained in preparative yields using L-pyroglutamic acid or L-proline as catalyst.
Lithium Bromide/Triethylamine Induced Cycloaddition of N-Alkylidene 2-Amino Esters and Amides to Electron-Deficient Olefins with High Regio- and Stereoselectivity
Tsuge, Otohiko,Kanemasa, Shuji,Yoshioka, Manabu
, p. 1384 - 1391 (2007/10/02)
The imines of 2-amino esters and amides derived from glycine, alanine, and valine are deprotonated by the action of a lithium halide and triethylamine (or DBU).The resulting anionic intermediates undergo highly regio- and stereoselective cycloadditions with a variety of olefins activated by carbonyl-type substituents to produce stereochemically defined derivatives of proline esters or amides.The scope and limitations of this novel cycloaddition are discussed.
