19766-29-1Relevant academic research and scientific papers
Reaction of lactim ethers and lactim sulfides with electrophiles: Attack at nitrogen followed by ring-opening under neutral conditions
Anbazhagan, Mariappan,Dixit, Arun N.,Rajappa, Srinivasachari
, p. 2421 - 2424 (1997)
Electrophilic push-pull molecules react at the nitrogen of lactim ethers and lactim sulfides; subsequent hydrolysis gives ring-opened products in good yields.
A new and simple method for the synthesis of highly functionalised pyrrolizidines, indolizidines and pyrroloazepines
O'Gorman, Paul A.,Chen, Ting,Cross, Hannah E.,Naeem, Saleena,Pitard, Arnaud,Qamar, M. Ilyas,Hemming, Karl
body text, p. 6316 - 6319 (2009/04/06)
The reaction of 5-, 6- and 7-membered cyclic thioimidates with cyclopropenones gives access to highly functionalised pyrrolizidines, indolizidines and pyrroloazepines via a formal [3+2] cycloaddition process.
Organoaluminum-Promoted Beckmann Rearrangement of Oxime Sulfonates
Maruoka, Keiji,Miyazaki, Tohru,Ando, Mamoru,Matsumura, Yasushi,Sakane, Soichi,et al.
, p. 2831 - 2843 (2007/10/02)
The Beckmann rearrangement of oxime sulfonates with simultaneous nucleophilic trapping of the intermediary iminocarbocation by organoaluminum reagents is described.This process provides a new and highly efficient route to imino thioethers, imino selenoethers, imino nitriles, and α-alkylated amines starting from oxime sulfonates by the use of dialkylaluminum thiolates, selenolates, diethylaluminum chloride-trimethylsilyl cyanide, and trialkylaluminum-diisobutylaluminum hydride systems, respectively.The present organoaluminum-promoted Beckmann rearrangement of oxime sulfonates has been successfully applied to the synthesis of naturally occuring alkaloids, pumiliotoxin C and solenopsin A and B, in stereoselective fashion.Moreover, α,α-dialkylation of amines can be realized by the successive treatment of oxime sulfonates with trialkylaluminum followed by allylic or propargylic Grignard reagents in synthetically useful yields.
