Azomethine, Carbonyl and Thiocarbonyl Ylides — Generation of Azomethine Ylides by Condensation of Aldehydes with N-Substituted α-Amino Esters

ChemInform ◽  
2004 ◽  
Vol 35 (22) ◽  
Author(s):  
M. Nyerges ◽  
L. Toke
Keyword(s):  
Azomethine Ylides ◽  
Amino Esters

Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines

Synlett ◽  
2007 ◽  
Vol 2007 (08) ◽  
pp. 1284-1288
Author(s):  
Sandrine Deloisy ◽  
Adrien Soret ◽  
Régis Guillot ◽  
Gérard Rousseau ◽  
Luis Blanco
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Esters

Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines.

ChemInform ◽  
2007 ◽  
Vol 38 (38) ◽  
Author(s):  
Adrien Soret ◽  
Regis Guillot ◽  
Gerard Rousseau ◽  
Luis Blanco ◽  
Sandrine Deloisy
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Esters

scholarly journals Simple Generation of Ester-Stabilized Azomethine Ylides from 2-Amino Esters and Carbonyl Compounds. Stereochemistry of Their Cycloadditions

1987 ◽  
Vol 60 (11) ◽  
pp. 4067-4078 ◽  
Author(s):  
Otohiko Tsuge ◽  
Shuji Kanemasa ◽  
Masayuki Ohe ◽  
Kiyotaka Yorozu ◽  
Shigeori Takenaka ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Azomethine Ylides ◽  
Amino Esters ◽  
Stabilized Azomethine Ylides

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-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 bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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