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
Hauptverfasser: Liang, Hao, Zhou, Xiaotong, Zheng, Liyao, Wang, Jun
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01678