Theoretical Study of the 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides. A DFT Study of Reaction between Trifluoromethyl Thiomethyl Azomethine Ylide and Acronitrile

1999 ◽  
Vol 64 (11) ◽  
pp. 3922-3929 ◽  
Author(s):  
Luis R. Domingo
Keyword(s):  
Theoretical Study ◽  
Dft Study ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

scholarly journals A General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides & Lactams

2021 ◽  
Author(s):  
Ken Yamazaki ◽  
Pablo Gabriel ◽  
Graziano Di Carmine ◽  
Julia Pedroni ◽  
Mirxan Farizyan ◽  
...  
Keyword(s):  
Density Functional ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Efficient Access ◽  
Stabilized Azomethine Ylides ◽  
Tertiary Amides

A new iridium-catalyzed reductive generation of both stabilized and unstabilized azomethine ylides and their application to functionalized pyrrolidine synthesis via [3+2] dipolar cycloaddition reactions is described. Proceeding under mild reaction conditions from both amide and lactam precursors possessing a suitably positioned electron-withdrawing or a trimethylsilyl group, using catalytic Vaska’s complex [IrCl(CO)(PPh3)2] and tetramethyldisiloxane (TMDS) as a terminal reductant, a broad range of (un)stabilized azomethine ylides were accessible. Subsequent, regio- and diastereoselective, inter- and intramolecular, dipolar cycloaddition reactions with variously substituted electron-poor alkenes enabled ready and efficient access to structurally complex pyrrolidine architectures. Density functional theory (DFT) calculations of the dipolar cycloaddition reactions uncovered an intimate balance between asynchronicity and interaction energies of transition structures which ultimately control the unusual selectivities observed in certain cases.

scholarly journals A General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides & Lactams

2021 ◽  
Author(s):  
Ken Yamazaki ◽  
Pablo Gabriel ◽  
Graziano Di Carmine ◽  
Julia Pedroni ◽  
Mirxan Farizyan ◽  
...  
Keyword(s):  
Density Functional ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Efficient Access ◽  
Stabilized Azomethine Ylides ◽  
Tertiary Amides

A new iridium-catalyzed reductive generation of both stabilized and unstabilized azomethine ylides and their application to functionalized pyrrolidine synthesis via [3+2] dipolar cycloaddition reactions is described. Proceeding under mild reaction conditions from both amide and lactam precursors possessing a suitably positioned electron-withdrawing or a trimethylsilyl group, using catalytic Vaska’s complex [IrCl(CO)(PPh3)2] and tetramethyldisiloxane (TMDS) as a terminal reductant, a broad range of (un)stabilized azomethine ylides were accessible. Subsequent, regio- and diastereoselective, inter- and intramolecular, dipolar cycloaddition reactions with variously substituted electron-poor alkenes enabled ready and efficient access to structurally complex pyrrolidine architectures. Density functional theory (DFT) calculations of the dipolar cycloaddition reactions uncovered an intimate balance between asynchronicity and interaction energies of transition structures which ultimately control the unusual selectivities observed in certain cases.

scholarly journals A General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides & Lactams

2021 ◽  
Author(s):  
Ken Yamazaki ◽  
Pablo Gabriel ◽  
Graziano Di Carmine ◽  
Julia Pedroni ◽  
Mirxan Farizyan ◽  
...  
Keyword(s):  
Density Functional ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Efficient Access ◽  
Stabilized Azomethine Ylides ◽  
Tertiary Amides

A new iridium-catalyzed reductive generation of both stabilized and unstabilized azomethine ylides and their application to functionalized pyrrolidine synthesis via [3+2] dipolar cycloaddition reactions is described. Proceeding under mild reaction conditions from both amide and lactam precursors possessing a suitably positioned electron-withdrawing or a trimethylsilyl group, using catalytic Vaska’s complex [IrCl(CO)(PPh3)2] and tetramethyldisiloxane (TMDS) as a terminal reductant, a broad range of (un)stabilized azomethine ylides were accessible. Subsequent, regio- and diastereoselective, inter- and intramolecular, dipolar cycloaddition reactions with variously substituted electron-poor alkenes enabled ready and efficient access to structurally complex pyrrolidine architectures. Density functional theory (DFT) calculations of the dipolar cycloaddition reactions uncovered an intimate balance between asynchronicity and interaction energies of transition structures which ultimately control the unusual selectivities observed in certain cases.

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.

1,3-Dipolar cycloaddition reactions of benzo[b]thiophene 1,1-dioxide with azomethine ylides

2006 ◽  
Vol 47 (29) ◽  
pp. 5139-5142 ◽  
Author(s):  
Nela Malatesti ◽  
Andrew N. Boa ◽  
Stephen Clark ◽  
Robert Westwood
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

Regio- and stereoselective 1,3-dipolar cycloaddition reactions between arylideneacetones and stabilized azomethine ylides obtained from ninhydrin and indenoquinoxalinones

2017 ◽  
Vol 53 (12) ◽  
pp. 1315-1323 ◽  
Author(s):  
Alexey Yu. Barkov ◽  
Nikolay S. Zimnitskiy ◽  
Igor B. Kutyashev ◽  
Vladislav Yu. Korotaev ◽  
Vyacheslav Ya. Sosnovskikh
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Stabilized Azomethine Ylides

1,3-Dipolar cycloaddition reactions of azomethine ylides with seven-membered cyclic N-sulfony imines access to polycyclic sulfonamides

Tetrahedron ◽  
2021 ◽  
Vol 77 ◽  
pp. 131766
Author(s):  
Kai-Kai Wang ◽  
Yan-Li Li ◽  
Ying-Jie Lv ◽  
Rong-Hua Shen ◽  
Wei Zhao ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions
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