Intramolecular ring-opening from a CO2-derived nucleophile as the origin of selectivity for 5-substituted oxazolidinone from the (salen)Cr-catalyzed [aziridine + CO2] coupling

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The (salen) Cr-catalyzed [aziridine + CO2] coupling to form oxazolidinone was found to exhibit excellent selectivity for the 5-substituted oxazolidinone product in the absence of any cocatalyst. Quantum mechanical calculations suggest that the preferential opening of the substituted C-N bond of the aziridine over the unsubstituted C-N bond is a key factor for this selectivity, a result that is supported by experiment with several phenyl-substituted aziridines. In the presence of external nucleophile such as dimethyl aminopyridine (DMAP), the reaction changes pathway and the ring-opening process is regulated by the steric demand of the nucleophile.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2015
Language
English
Article Type
Article
Keywords

ANTI-ALDOL REACTIONS; CARBON-DIOXIDE; HIGHLY EFFICIENT; ALTERNATING COPOLYMERIZATION; N-ACYLOXAZOLIDINONES; DENSITY FUNCTIONALS; CHEMICAL FIXATION; SALEN COMPLEXES; PROPYLENE-OXIDE; CATALYSTS

Citation

CHEMICAL SCIENCE, v.6, no.2, pp.1293 - 1300

ISSN
2041-6520
DOI
10.1039/c4sc02785j
URI
http://hdl.handle.net/10203/203289
Appears in Collection
CH-Journal Papers(저널논문)
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