Intramolecular 1, 3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles

…, AJ Kouklis, CH Heathcock

Index: Henke, Brad R.; Kouklis, Andrew J.; Heathcock, Clayton H. Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7056 - 7066

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Citation Number: 83

Abstract

The scope and limitations of the intramolecular l, &dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo [3.3. 0] ...