124948-53-4Relevant articles and documents
1,3-Dipolar Cycloaddition of Imidate Ylides on Imino-Alcohols: Synthesis of New Imidazolones Using Solvent Free Conditions.
Lerestif, Jean Michel,Perrocheau, Jacques,Tonnard, Francois,Bazureau, Jean Pierre,Hamelin, Jack
, p. 6757 - 6774 (1995)
Imidates derived from α-amino esters as potential azomethine ylides, undergo 1,3-dipolar cycloaddition with imino-alcohols, in tautomeric equilibrium with 1,3-oxazolidines, without solvent at 70 deg C or under microwave irradiation.This reaction leads to a wide range of novel polyfunctionalized 4-yliden-2-imidazolin-5-ones in good yields with short reaction times.The reactivity of these imidates derived from α-amino esters with imino-alcohols is rationalized from the energy of the Frontier Molecular Orbitals (FMO) determined by semi-empirical PM3 calculations : the reaction is controlled by the interaction HOMO(1,3-dipole) - LUMO(dipolarophile) and the second order perturbation energy calculations are in agreement with the experimental reaction orientation.