Stereocontrolled, Divergent, Al(III)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2

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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.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-08
Language
English
Article Type
Article
Keywords

HYDROLYTIC KINETIC RESOLUTION; CARBON-DIOXIDE; CYCLIC CARBONATES; SELECTIVE FORMATION; EPOXIDES; COPOLYMERIZATION; CATALYSTS; CYCLOADDITION; COMPLEXES; MECHANISM

Citation

ORGANIC LETTERS, v.20, no.16, pp.5036 - 5039

ISSN
1523-7060
DOI
10.1021/acs.orglett.8b02186
URI
http://hdl.handle.net/10203/245923
Appears in Collection
CH-Journal Papers(저널논문)
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