87813-01-2Relevant academic research and scientific papers
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.
N-(TRIMETHYLSILYLMETHYL)AMINOMETHYL ETHERS AS AZOMETHINE YLIDE SYNTHONS. A NEW AND CONVENIENT ACCESS TO PYRROLIDINE DERIVATIVES
Hosomi, Akira,Sakata, Yasuyuki,Sakurai, Hideki
, p. 1117 - 1120 (2007/10/02)
The title compounds, readily prepared from (trimethylsilylmethyl)amines, formaldehyde and an alcohol, react with electron deficient alkenes in the presence of iodosilane or silyl triflate in combination with cesium fluoride to give the corresponding pyrrolidine derivatives stereospecifically in excellent yield.
SYNTHESIS OF PYRROLIDINES USING AN α-CYANOAMINOSILANE AS AN AZOMETHINE YLIDE EQUIVALENT
Padwa, Albert,Chen, Yon-Yih
, p. 3447 - 3450 (2007/10/02)
The potential of α-cyanoaminosilane (3) to act as an azomethine ylide equivalent is illustrated by its treatment with silver fluoride in the presence of electron deficient olefins to give substituted pyrrolidines in high yield.
