Enantioselective Organocatalytic Desymmetrization of Cyclopentene-1,3-diones through Formal C(sp2)–H Amidation
An enantioselective organocatalytic desymmetrization of 2,2-disubstituted cyclopentene-1,3-diones via a formal C(sp2)–H amidation is reported. The reaction was carried out with N-methoxy amide as the nitrogen source and commercially available cinchonidine as the catalyst under mild reaction conditi...
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Veröffentlicht in: | Journal of organic chemistry 2019-09, Vol.84 (17), p.11306-11315 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | An enantioselective organocatalytic desymmetrization of 2,2-disubstituted cyclopentene-1,3-diones via a formal C(sp2)–H amidation is reported. The reaction was carried out with N-methoxy amide as the nitrogen source and commercially available cinchonidine as the catalyst under mild reaction conditions, releasing methanol as the only byproduct. It provides an efficient way to synthesize enantioenriched chiral cyclopentenyl amines bearing an all-carbon quaternary stereogenic carbon center. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b01678 |