Synthesis of Oxazolidinones and 1,2‐Diamines from N‐Alkyl Aziridines.

Abstract

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Valorization of Carbon Dioxide into Oxazolidinones by Reaction with Aziridines

“…In the late 20 th and early 21 st Century, numerous metal complexes and salts such as LiI [24,25] (2, Scheme 3), alkali metal halides [26] (3, Scheme 3) and organotin complexes [27] (4, Scheme 3) were the first metal catalysts tested in the transformation of CO2 into oxazolidinones. These catalysts required high catalytic loadings (at least 25 mol% in the case of LiI), high pressures of CO2 (50-55 bar in the case of organoantimony salts) and reported poor isomer selectively.…”

“…In 2008, Li performed detailed DFT analysis [42] of the reaction mechanism between aziridines and CO2 conversion into oxazolidinones, via Pinhas's LiI catalytic route. [24,25] Li concluded that changing alkyl substituents on the three membered ring strongly affects regioselectivity, whereas changing groups on the nitrogen atom seemed to have little to no effect at all. [42] Li proposed that when simple alkyl groups are present on the three membered ring (with functional groups on the nitrogen) ring-opening only occurs at the less sterically hindered carbon-nitrogen bond.…”