101046-33-7Relevant academic research and scientific papers
A New and Efficient Strategy for Non-stabilized Azomethine Ylide via Photoinduced Electron Transfer (PET) Initiated Sequential Double Desilylation
Pandey, Ganesh,Lakshmaiah, G.,Kumaraswamy, G.
, p. 1313 - 1314 (2007/10/02)
A practical approach for generating non-stabilized azomethine ylide by PTE initiation is generated.
Synthetic Application of Cyanoaminosilanes as Azomethine Ylide Equivalents
Padwa, Albert,Chen, Yon-Yih,Dent, William,Nimmesgern, Hildegard
, p. 4006 - 4014 (2007/10/02)
A series of α-cyanoaminosilanes have been found to act as azomethine ylide equivalents.Treatment of these compounds with silver fluoride in the presence of electron-dificient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield.It was found that N-benzyl-N-(cyanomethyl)-N-amine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate.The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction.The cycloaddition behavior of an unsymmetrically substituted α-cyanosilylamine with methyl propiolate was also examined and found to react with high overall regioselectivity.The synthetic utility of cyanoaminosilanes as azomethine ylide equivalents was demonstrated by the preparation of a Reniera isoindole alkaloid.The key step in the synthesis involved the reaction of 2-methyl-3-methoxyquinone with N-methyl-N-(cyanomethyl)-N-amine in the presence of silver fluoride to give 2,5-dimethyl-6-methoxy-2H-isoindole-4,7-dione in good yield.
Trifluoroacetic Acid-Catalyzed 1,3-Cycloaddition of the Simplest Iminium Ylide Leading to 3- or 3,4-Substituted Pyrrolidines and 2,5-Dihydropyrroles
Terao, Yoshiyasu,Kotaki, Hiromi,Imai, Nobuyuki,Achiwa, Kazuo
, p. 2762 - 2766 (2007/10/02)
The 1,3-dipolar cycloaddition of an intermediary iminium ylide formed from N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine to conjugated olefinic and acetylenic dipolarophiles in the presence of a catalytic amount of trifluoroacetic acid has been found to give 3- or 3,4-substituted pyrrolidines and 2,5-dihydropyrroles.
