115074-67-4Relevant academic research and scientific papers
Stable configuration of Ester-Stabilized Azomethine Ylides. Stabilization of anti-Form by 1,5-Dipolar Interaction and of syn-Form by Hydrogen Bonding
Tsuge, Otohiko,Kanemasa, Shuji,Ohe, Masayuki,Yorozu, Kiyotaka,Takenaka, Shigeori,Ueno, Kazunori
, p. 1271 - 1274 (1986)
Stable configuration of ester-stabilized azomethine ylides is found to depend upon the substituent on the ylide nitrogen.Thus, N-substituted azomethine ylides derived from N-substituted 2-amino-acetates and carbonyl compounds undergo cycloaddition with ol
Simple Generation of Ester-Stabilized Azomethine Ylides from 2-Amino Esters and Carbonyl Compounds. Stereochemistry of Their Cycloadditions
Tsuge, Otohiko,Kanemasa, Shuji,Ohe, Masayuki,Yorozu, Kiyotaka,Takenaka, Shigeori,Ueno, Kazunori
, p. 4067 - 4078 (2007/10/02)
Condensation of 2-amino esters with carbonyl compounds leads to simple generation of ester-stabilized azomethine ylides which are trapped by olefinic dipolarophiles as cycloadducts.Anti ylides are exclusively involved in the cycloadditions when N-substituted 2-amino esters are employed for the ylide generation, while syn ylides from N-unsubstituted 2-amino esters.Relative stability among all possible ylide isomers has been inspected and the selective involvement of particular ylidic forms has been explained on the ground of 1,5-dipole interaction or hydrogen bonding stabilization.Endo- and exo-selectivity of the cycloadditions is also discussed.
