On February 18, 2022, Ondari, Mark E.; Klosin, Jerzy; Kruper, William R.; Lysenko, Ivan; Thomas, Pulikkottil J.; Cheng, Kevin; Abboud, Khalil A.; Kruper, William J. published an article.Quality Control of 2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione The title of the article was Diol-Ritter Reaction: Regio- and Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation. And the article contained the following:
Herein, a mechanism-based study of the less known diol-Ritter reaction had provided a highly regioselective procedure for the synthesis of 1-vic-amido-2-esters from either terminal epoxides or 1,2-diols via Lewis Acid-catalyzed monoesterification. When treated with stoichiometric Lewis Acid catalyst (BF3), these diol monoesters form dioxonium cation intermediates that are ring-opened with nitrile nucleophiles to form nitrilium intermediates, which undergo rapid and irreversible hydration to give the desired amidoesters. Diester byproduct formation was irreversible and appears to occur through a disproportionation of diol monoester. With chiral epoxide starting materials, the formation of amidoester occurs with retention of configuration and no apparent erosion of optical purity as determined by single-crystal X-ray analyzes and chiral chromatog., resp. The direct access to chiral vic-amidoesters was especially practical with regard to the synthesis of Gram-pos., antibacterial, oxazolidinone analogs of the Zyvox antimicrobial family. The experimental process involved the reaction of 2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione(cas: 5455-98-1).Quality Control of 2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione
The Article related to protected vicinal aminoalc regioselective stereoselective preparation, General Organic Chemistry: Synthetic Methods and other aspects.Quality Control of 2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics