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

Shang, Ming; Wang, Xiaoxu; Koo, Seung Moh; Youn, Jennifer; Chan, Jessica Z.; Yao, Wenzhi; Hastings, Brian T.; Wasa, Masayuki

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

2017

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.

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