Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides

2011 ◽  
Vol 47 (24) ◽  
pp. 6784 ◽  
Author(s):  
Javier Adrio ◽  
Juan C. Carretero
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Metal Catalyzed

scholarly journals Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 55 (80) ◽  
pp. 11979-11991 ◽  
Author(s):  
Javier Adrio ◽  
Juan C. Carretero
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Feature Article ◽  
Catalytic Asymmetric ◽  
Metal Catalyzed

The aim of this feature article is to show the stereochemical versatility of the metal-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

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.

ChemInform Abstract: Oligopyrrole Synthesis by 1,3-Dipolar Cycloaddition of Azomethine Ylides with Bissulfonyl Ethylenes.

ChemInform ◽  
2008 ◽  
Vol 39 (15) ◽  
Author(s):  
Ana Lopez-Perez ◽  
Rocio Robles-Machin ◽  
Javier Adrio ◽  
Juan Carlos Carretero
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition

scholarly journals Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides

2016 ◽  
Vol 22 (14) ◽  
pp. 4952-4959 ◽  
Author(s):  
Alberto Ponce ◽  
Inés Alonso ◽  
Javier Adrio ◽  
Juan C. Carretero
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition

Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles

2016 ◽  
Vol 52 (60) ◽  
pp. 9458-9461 ◽  
Author(s):  
Kang Liu ◽  
Yong Xiong ◽  
Zuo-Fei Wang ◽  
Hai-Yan Tao ◽  
Chun-Jiang Wang
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition

An unprecedented Ag(i)-catalyzed ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford heterocycles bearing both methylisoxazole and pyrrolidine moieties.

Intramolecular 1,3-Dipolar Cycloaddition of Geminal Difluoro Azomethine Ylides at Multiple Carbon—Carbon Bonds.

ChemInform ◽  
2005 ◽  
Vol 36 (45) ◽  
Author(s):  
M. S. Novikov ◽  
A. F. Khlebnikov ◽  
I. V. Voznyi ◽  
O. V. Besedina ◽  
R. R. Kostikov
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds
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