Amine-catalyzed site- and stereo-selective coupling of epoxy amines and carbon dioxide to construct oxazolidinones
A non-metal catalyzed coupling of epoxy amines and CO 2 was achieved using readily available tertiary amines, under atmospheric pressure of CO 2 in the absence of any co-catalyst or additive. A high selectivity was obtained, as oxazolidinones were formed almost exclusively in most cases, while negli...
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Veröffentlicht in: | Organic Chemistry Frontiers 2022-08, Vol.9 (16), p.4294-4300 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A non-metal catalyzed coupling of epoxy amines and CO
2
was achieved using readily available tertiary amines, under atmospheric pressure of CO
2
in the absence of any co-catalyst or additive. A high selectivity was obtained, as oxazolidinones were formed almost exclusively in most cases, while negligible amounts of cyclic carbonates were detected. Overall 22 oxazolidinones bearing alkyl, halo, nitro, and methoxy-substituted aryl groups were produced in 75–99% yields under mild conditions (1 bar CO
2
, 60–80 °C). This strategy led to 100% configuration inversion and was applied to synthesize the chiral antibiotic drug linezolid. With the aid of kinetic and DFT studies, the role of tertiary amines was found as a nucleophile to cause ring-opening of epoxides, which forms alkoxides as key intermediates. |
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ISSN: | 2052-4129 2052-4110 2052-4129 2052-4110 |
DOI: | 10.1039/D2QO00583B |