125557-71-3Relevant academic research and scientific papers
Generation of an N-Sodioazomethine Ylide and Its Cycloadditions with α,β-Unsaturated Esters
Kanemasa, Shuji,Yoshioka, Manabu,Tsuge, Otohiko
, p. 2196 - 2200 (1989)
Treatment of methyl 2-(benzylideneamino)propanoate with sodium hydride in THF generates an N-sodioazomethine ylide, which shows a very poor stereoselectivity in the cycloaddition with methyl acrylate.However, addition of such a base as triethylamine or t-
Lithium Bromide/Triethylamine Induced Cycloaddition of N-Alkylidene 2-Amino Esters and Amides to Electron-Deficient Olefins with High Regio- and Stereoselectivity
Tsuge, Otohiko,Kanemasa, Shuji,Yoshioka, Manabu
, p. 1384 - 1391 (2007/10/02)
The imines of 2-amino esters and amides derived from glycine, alanine, and valine are deprotonated by the action of a lithium halide and triethylamine (or DBU).The resulting anionic intermediates undergo highly regio- and stereoselective cycloadditions with a variety of olefins activated by carbonyl-type substituents to produce stereochemically defined derivatives of proline esters or amides.The scope and limitations of this novel cycloaddition are discussed.
