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Published on: June 23, 2019
Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2
Yuseop Lee1, Jonghoon Choi1, Hyunwoo Kim1
1Department of Chemistry , Korea Advanced Institute of Science and Technology (KAIST) , Daejeon 34141 , Korea.
Abstract:
A divergent coupling reaction was achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A gram-scale production of Linezolid was successfully achieved.
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