Frustrated Lewis Acid/Brønsted Base Catalysts for Direct Enantioselective α‑Amination of Carbonyl Compounds

A method for enantioselective direct α-amination reaction catalyzed by a sterically “frustrated” Lewis acid/Brønsted base complex is disclosed. Cooperative functioning of the Lewis acid and Brønsted base components gives rise to in situ enolate generation from monocarbonyl compounds. Subsequent reac...

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Veröffentlicht in:Journal of the American Chemical Society 2017-01, Vol.139 (1), p.95-98
Hauptverfasser: Shang, Ming, Wang, Xiaoxu, Koo, Seung Moh, Youn, Jennifer, Chan, Jessica Z, Yao, Wenzhi, Hastings, Brian T, Wasa, Masayuki
Format: Artikel
Sprache:eng
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Zusammenfassung:A method for enantioselective direct α-amination reaction catalyzed by a sterically “frustrated” Lewis acid/Brønsted base complex is disclosed. Cooperative functioning of the Lewis acid and Brønsted base components gives rise to in situ enolate generation from monocarbonyl compounds. Subsequent reaction with hydrogen-bond activated dialkyl azodicarboxylates delivers α-aminocarbonyl compounds in high enantiomeric purity.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b11908